Product Name

  • Name

    RESINIFERATOXIN

  • EINECS
  • CAS No. 57444-62-9
  • Article Data2
  • CAS DataBase
  • Density 1.35g/cm3
  • Solubility
  • Melting Point
  • Formula C37H40 O9
  • Boiling Point 768.7°Cat760mmHg
  • Molecular Weight 628.719
  • Flash Point 240.3°C
  • Transport Information
  • Appearance
  • Safety A poison by intracerebral route. When heated to decomposition it emits acrid smoke and irritating vapors.
  • Risk Codes R25; R35
  • Molecular Structure Molecular Structure of 57444-62-9 (RESINIFERATOXIN)
  • Hazard Symbols A poison.
  • Synonyms Daphnetoxin,6,7-deepoxy-6,7-didehydro-5-deoxy-21-dephenyl-21-(phenylmethyl)-,20-(4-hydroxy-3-methoxybenzeneacetate); (+)-Resiniferatoxin; Benzeneaceticacid, 4-hydroxy-3-methoxy-,[3a,3b,6,6a,9a,10,11,11a-octahydro-6a-hydroxy-8,10-dimethyl-11a-(1-methylethenyl)-7-oxo-2-(phenylmethyl)-7H-2,9b-epoxyazuleno[5,4-e]-1,3-benzodioxol-5-yl]methylester, [2S-(2a,3ab,3bb,6ab,9aa,9ba,10a,11ab)]-; Resiniferatoxin
  • PSA 120.75000
  • LogP 4.74470

Synthetic route

2-(4-((tert-butyldimethylsilyl)oxy)-3-methoxyphenyl)acetic acid
1344662-01-6

2-(4-((tert-butyldimethylsilyl)oxy)-3-methoxyphenyl)acetic acid

C31H39ClO5Si

C31H39ClO5Si

resiniferatoxin
57444-62-9

resiniferatoxin

Conditions
ConditionsYield
Stage #1: 2-(4-((tert-butyldimethylsilyl)oxy)-3-methoxyphenyl)acetic acid; C31H39ClO5Si With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 5.66667h;
Stage #2: With tetrabutyl ammonium fluoride In tetrahydrofuran at 0℃; for 0.583333h;		92%
Homovanillic acid
306-08-1

Homovanillic acid

Resininiferonol-9-13-14-ortho-phenyl acetate

Resininiferonol-9-13-14-ortho-phenyl acetate

resiniferatoxin
57444-62-9

resiniferatoxin

Conditions
ConditionsYield
With di-tert-butyl-diazodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 1h; Mitsunobu reaction;67%
C17H28O5

C17H28O5

resiniferatoxin
57444-62-9

resiniferatoxin

Conditions
ConditionsYield
Multi-step reaction with 32 steps
1.1: Dowex 50W / tetrahydrofuran; water / 12 h / 90 °C
2.1: pyridine / dichloromethane / 1 h / 0 - 20 °C
3.1: (+)-CSA / benzene / 2 h / 20 °C / Inert atmosphere
4.1: triethylamine / dichloromethane / 0.75 h / 20 °C / Inert atmosphere
5.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 °C
5.2: 0.42 h
6.1: lead(IV) tetraacetate; potassium carbonate / toluene / 1.17 h / 0 - 20 °C
7.1: triethylamine / dichloromethane / 1.25 h / 0 °C
8.1: dmap / toluene / 1.5 h / 20 °C / Darkness
9.1: sodium hydrogencarbonate / toluene / 0.5 h / 20 °C / Irradiation
10.1: potassium carbonate / methanol / 7.5 h / 0 °C
11.1: acetic anhydride; dimethyl sulfoxide / 2 h / 35 °C
12.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol / 0.17 h / -78 °C
13.1: 2,6-dimethylpyridine / water; dichloromethane / 0.5 h / 0 °C
14.1: 1,1'-azobis(1-cyanocyclohexanenitrile) / chlorobenzene / 0.5 h / Reflux; Inert atmosphere
15.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
16.1: triethylamine / dichloromethane / 1.5 h / 0 °C
17.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / hexane; dichloromethane / 0.5 h / 0 °C
18.1: diisobutylaluminium hydride / hexane; dichloromethane / 1 h / -93 °C / Inert atmosphere
18.2: (+)-CSA / 0.33 h / 50 °C
19.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 20 °C
20.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C / Inert atmosphere
20.2: 0.5 h / 20 °C / Inert atmosphere
21.1: 5,5-dimethyl-1,3-cyclohexadiene / 1.5 h / 110 °C / Inert atmosphere
22.1: tri-n-butyl-tin hydride; 1,1'-azobis(1-cyanocyclohexanenitrile) / 5,5-dimethyl-1,3-cyclohexadiene / 0.17 h / 180 °C / Inert atmosphere; Microwave irradiation
23.1: hydrogenchloride / water; methanol / 3.5 h / 30 °C
23.2: 1.5 h
24.1: dmap; 2-azatricyclo[3.3.1.13,7]dec-2-yloxidanyl; [2,2]bipyridinyl; copper(l) chloride / acetonitrile / 0.5 h / 0 °C
25.1: dmap / tetrahydrofuran; toluene / 2 h / 0 °C
26.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 20 °C
27.1: L-Selectride / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere
28.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
28.2: 0.33 h / -20 °C / Inert atmosphere
29.1: dmap; 1,4-diaza-bicyclo[2.2.2]octane / acetonitrile / 76 h / 110 °C
30.1: N-Bromosuccinimide / tetrahydrofuran / 0.83 h / 0 °C
31.1: selenium(IV) oxide / tert-butyl alcohol / 80 °C
31.2: 0.42 h / 150 °C
31.3: 0.5 h / 0 - 20 °C
32.1: caesium carbonate / N,N-dimethyl-formamide / 5.67 h / 20 °C
32.2: 0.58 h / 0 °C
View Scheme
Multi-step reaction with 33 steps
1.1: Dowex 50W / tetrahydrofuran; water / 12 h / 90 °C
2.1: pyridine / dichloromethane / 1 h / 0 - 20 °C
3.1: (+)-CSA / benzene / 2 h / 20 °C / Inert atmosphere
4.1: triethylamine / dichloromethane / 0.75 h / 20 °C / Inert atmosphere
5.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 °C
5.2: 0.42 h
6.1: lead(IV) tetraacetate; potassium carbonate / toluene / 1.17 h / 0 - 20 °C
7.1: triethylamine / dichloromethane / 1.25 h / 0 °C
8.1: dmap / toluene / 1.5 h / 20 °C / Darkness
9.1: sodium hydrogencarbonate / toluene / 0.5 h / 20 °C / Irradiation
10.1: potassium carbonate / methanol / 7.5 h / 0 °C
11.1: acetic anhydride; dimethyl sulfoxide / 2 h / 35 °C
12.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol / 0.17 h / -78 °C
13.1: 2,6-dimethylpyridine / water; dichloromethane / 0.5 h / 0 °C
14.1: 1,1'-azobis(1-cyanocyclohexanenitrile) / chlorobenzene / 0.5 h / Reflux; Inert atmosphere
15.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
16.1: triethylamine / dichloromethane / 1.5 h / 0 °C
17.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / hexane; dichloromethane / 0.5 h / 0 °C
18.1: diisobutylaluminium hydride / hexane; dichloromethane / 1 h / -93 °C / Inert atmosphere
18.2: (+)-CSA / 0.33 h / 50 °C
19.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 20 °C
20.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C / Inert atmosphere
20.2: 0.5 h / 20 °C / Inert atmosphere
21.1: 5,5-dimethyl-1,3-cyclohexadiene / 1.5 h / 110 °C / Inert atmosphere
22.1: tri-n-butyl-tin hydride; 1,1'-azobis(1-cyanocyclohexanenitrile) / 5,5-dimethyl-1,3-cyclohexadiene / 0.17 h / 180 °C / Inert atmosphere; Microwave irradiation
23.1: hydrogenchloride / water; methanol / 3.5 h / 30 °C
23.2: 1.5 h
24.1: hydrogenchloride / methanol; water / 3.5 h / 30 °C
24.2: 1.5 h
25.1: dmap; 2-azatricyclo[3.3.1.13,7]dec-2-yloxidanyl; [2,2]bipyridinyl; copper(l) chloride / acetonitrile / 0.5 h / 0 °C
26.1: dmap / tetrahydrofuran; toluene / 2 h / 0 °C
27.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 20 °C
28.1: L-Selectride / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere
29.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
29.2: 0.33 h / -20 °C / Inert atmosphere
30.1: dmap; 1,4-diaza-bicyclo[2.2.2]octane / acetonitrile / 76 h / 110 °C
31.1: N-Bromosuccinimide / tetrahydrofuran / 0.83 h / 0 °C
32.1: selenium(IV) oxide / tert-butyl alcohol / 80 °C
32.2: 0.42 h / 150 °C
32.3: 0.5 h / 0 - 20 °C
33.1: caesium carbonate / N,N-dimethyl-formamide / 5.67 h / 20 °C
33.2: 0.58 h / 0 °C
View Scheme
C12H20O5

C12H20O5

resiniferatoxin
57444-62-9

resiniferatoxin

Conditions
ConditionsYield
Multi-step reaction with 31 steps
1.1: pyridine / dichloromethane / 1 h / 0 - 20 °C
2.1: (+)-CSA / benzene / 2 h / 20 °C / Inert atmosphere
3.1: triethylamine / dichloromethane / 0.75 h / 20 °C / Inert atmosphere
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 °C
4.2: 0.42 h
5.1: lead(IV) tetraacetate; potassium carbonate / toluene / 1.17 h / 0 - 20 °C
6.1: triethylamine / dichloromethane / 1.25 h / 0 °C
7.1: dmap / toluene / 1.5 h / 20 °C / Darkness
8.1: sodium hydrogencarbonate / toluene / 0.5 h / 20 °C / Irradiation
9.1: potassium carbonate / methanol / 7.5 h / 0 °C
10.1: acetic anhydride; dimethyl sulfoxide / 2 h / 35 °C
11.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol / 0.17 h / -78 °C
12.1: 2,6-dimethylpyridine / water; dichloromethane / 0.5 h / 0 °C
13.1: 1,1'-azobis(1-cyanocyclohexanenitrile) / chlorobenzene / 0.5 h / Reflux; Inert atmosphere
14.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
15.1: triethylamine / dichloromethane / 1.5 h / 0 °C
16.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / hexane; dichloromethane / 0.5 h / 0 °C
17.1: diisobutylaluminium hydride / hexane; dichloromethane / 1 h / -93 °C / Inert atmosphere
17.2: (+)-CSA / 0.33 h / 50 °C
18.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 20 °C
19.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C / Inert atmosphere
19.2: 0.5 h / 20 °C / Inert atmosphere
20.1: 5,5-dimethyl-1,3-cyclohexadiene / 1.5 h / 110 °C / Inert atmosphere
21.1: tri-n-butyl-tin hydride; 1,1'-azobis(1-cyanocyclohexanenitrile) / 5,5-dimethyl-1,3-cyclohexadiene / 0.17 h / 180 °C / Inert atmosphere; Microwave irradiation
22.1: hydrogenchloride / water; methanol / 3.5 h / 30 °C
22.2: 1.5 h
23.1: dmap; 2-azatricyclo[3.3.1.13,7]dec-2-yloxidanyl; [2,2]bipyridinyl; copper(l) chloride / acetonitrile / 0.5 h / 0 °C
24.1: dmap / tetrahydrofuran; toluene / 2 h / 0 °C
25.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 20 °C
26.1: L-Selectride / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere
27.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
27.2: 0.33 h / -20 °C / Inert atmosphere
28.1: dmap; 1,4-diaza-bicyclo[2.2.2]octane / acetonitrile / 76 h / 110 °C
29.1: N-Bromosuccinimide / tetrahydrofuran / 0.83 h / 0 °C
30.1: selenium(IV) oxide / tert-butyl alcohol / 80 °C
30.2: 0.42 h / 150 °C
30.3: 0.5 h / 0 - 20 °C
31.1: caesium carbonate / N,N-dimethyl-formamide / 5.67 h / 20 °C
31.2: 0.58 h / 0 °C
View Scheme
Multi-step reaction with 32 steps
1.1: pyridine / dichloromethane / 1 h / 0 - 20 °C
2.1: (+)-CSA / benzene / 2 h / 20 °C / Inert atmosphere
3.1: triethylamine / dichloromethane / 0.75 h / 20 °C / Inert atmosphere
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 °C
4.2: 0.42 h
5.1: lead(IV) tetraacetate; potassium carbonate / toluene / 1.17 h / 0 - 20 °C
6.1: triethylamine / dichloromethane / 1.25 h / 0 °C
7.1: dmap / toluene / 1.5 h / 20 °C / Darkness
8.1: sodium hydrogencarbonate / toluene / 0.5 h / 20 °C / Irradiation
9.1: potassium carbonate / methanol / 7.5 h / 0 °C
10.1: acetic anhydride; dimethyl sulfoxide / 2 h / 35 °C
11.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol / 0.17 h / -78 °C
12.1: 2,6-dimethylpyridine / water; dichloromethane / 0.5 h / 0 °C
13.1: 1,1'-azobis(1-cyanocyclohexanenitrile) / chlorobenzene / 0.5 h / Reflux; Inert atmosphere
14.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
15.1: triethylamine / dichloromethane / 1.5 h / 0 °C
16.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / hexane; dichloromethane / 0.5 h / 0 °C
17.1: diisobutylaluminium hydride / hexane; dichloromethane / 1 h / -93 °C / Inert atmosphere
17.2: (+)-CSA / 0.33 h / 50 °C
18.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 20 °C
19.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C / Inert atmosphere
19.2: 0.5 h / 20 °C / Inert atmosphere
20.1: 5,5-dimethyl-1,3-cyclohexadiene / 1.5 h / 110 °C / Inert atmosphere
21.1: tri-n-butyl-tin hydride; 1,1'-azobis(1-cyanocyclohexanenitrile) / 5,5-dimethyl-1,3-cyclohexadiene / 0.17 h / 180 °C / Inert atmosphere; Microwave irradiation
22.1: hydrogenchloride / water; methanol / 3.5 h / 30 °C
22.2: 1.5 h
23.1: hydrogenchloride / methanol; water / 3.5 h / 30 °C
23.2: 1.5 h
24.1: dmap; 2-azatricyclo[3.3.1.13,7]dec-2-yloxidanyl; [2,2]bipyridinyl; copper(l) chloride / acetonitrile / 0.5 h / 0 °C
25.1: dmap / tetrahydrofuran; toluene / 2 h / 0 °C
26.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 20 °C
27.1: L-Selectride / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere
28.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
28.2: 0.33 h / -20 °C / Inert atmosphere
29.1: dmap; 1,4-diaza-bicyclo[2.2.2]octane / acetonitrile / 76 h / 110 °C
30.1: N-Bromosuccinimide / tetrahydrofuran / 0.83 h / 0 °C
31.1: selenium(IV) oxide / tert-butyl alcohol / 80 °C
31.2: 0.42 h / 150 °C
31.3: 0.5 h / 0 - 20 °C
32.1: caesium carbonate / N,N-dimethyl-formamide / 5.67 h / 20 °C
32.2: 0.58 h / 0 °C
View Scheme
C19H24O6

C19H24O6

resiniferatoxin
57444-62-9

resiniferatoxin

Conditions
ConditionsYield
Multi-step reaction with 30 steps
1.1: (+)-CSA / benzene / 2 h / 20 °C / Inert atmosphere
2.1: triethylamine / dichloromethane / 0.75 h / 20 °C / Inert atmosphere
3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 °C
3.2: 0.42 h
4.1: lead(IV) tetraacetate; potassium carbonate / toluene / 1.17 h / 0 - 20 °C
5.1: triethylamine / dichloromethane / 1.25 h / 0 °C
6.1: dmap / toluene / 1.5 h / 20 °C / Darkness
7.1: sodium hydrogencarbonate / toluene / 0.5 h / 20 °C / Irradiation
8.1: potassium carbonate / methanol / 7.5 h / 0 °C
9.1: acetic anhydride; dimethyl sulfoxide / 2 h / 35 °C
10.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol / 0.17 h / -78 °C
11.1: 2,6-dimethylpyridine / water; dichloromethane / 0.5 h / 0 °C
12.1: 1,1'-azobis(1-cyanocyclohexanenitrile) / chlorobenzene / 0.5 h / Reflux; Inert atmosphere
13.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
14.1: triethylamine / dichloromethane / 1.5 h / 0 °C
15.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / hexane; dichloromethane / 0.5 h / 0 °C
16.1: diisobutylaluminium hydride / hexane; dichloromethane / 1 h / -93 °C / Inert atmosphere
16.2: (+)-CSA / 0.33 h / 50 °C
17.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 20 °C
18.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C / Inert atmosphere
18.2: 0.5 h / 20 °C / Inert atmosphere
19.1: 5,5-dimethyl-1,3-cyclohexadiene / 1.5 h / 110 °C / Inert atmosphere
20.1: tri-n-butyl-tin hydride; 1,1'-azobis(1-cyanocyclohexanenitrile) / 5,5-dimethyl-1,3-cyclohexadiene / 0.17 h / 180 °C / Inert atmosphere; Microwave irradiation
21.1: hydrogenchloride / water; methanol / 3.5 h / 30 °C
21.2: 1.5 h
22.1: dmap; 2-azatricyclo[3.3.1.13,7]dec-2-yloxidanyl; [2,2]bipyridinyl; copper(l) chloride / acetonitrile / 0.5 h / 0 °C
23.1: dmap / tetrahydrofuran; toluene / 2 h / 0 °C
24.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 20 °C
25.1: L-Selectride / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere
26.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
26.2: 0.33 h / -20 °C / Inert atmosphere
27.1: dmap; 1,4-diaza-bicyclo[2.2.2]octane / acetonitrile / 76 h / 110 °C
28.1: N-Bromosuccinimide / tetrahydrofuran / 0.83 h / 0 °C
29.1: selenium(IV) oxide / tert-butyl alcohol / 80 °C
29.2: 0.42 h / 150 °C
29.3: 0.5 h / 0 - 20 °C
30.1: caesium carbonate / N,N-dimethyl-formamide / 5.67 h / 20 °C
30.2: 0.58 h / 0 °C
View Scheme
Multi-step reaction with 31 steps
1.1: (+)-CSA / benzene / 2 h / 20 °C / Inert atmosphere
2.1: triethylamine / dichloromethane / 0.75 h / 20 °C / Inert atmosphere
3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 °C
3.2: 0.42 h
4.1: lead(IV) tetraacetate; potassium carbonate / toluene / 1.17 h / 0 - 20 °C
5.1: triethylamine / dichloromethane / 1.25 h / 0 °C
6.1: dmap / toluene / 1.5 h / 20 °C / Darkness
7.1: sodium hydrogencarbonate / toluene / 0.5 h / 20 °C / Irradiation
8.1: potassium carbonate / methanol / 7.5 h / 0 °C
9.1: acetic anhydride; dimethyl sulfoxide / 2 h / 35 °C
10.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol / 0.17 h / -78 °C
11.1: 2,6-dimethylpyridine / water; dichloromethane / 0.5 h / 0 °C
12.1: 1,1'-azobis(1-cyanocyclohexanenitrile) / chlorobenzene / 0.5 h / Reflux; Inert atmosphere
13.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
14.1: triethylamine / dichloromethane / 1.5 h / 0 °C
15.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / hexane; dichloromethane / 0.5 h / 0 °C
16.1: diisobutylaluminium hydride / hexane; dichloromethane / 1 h / -93 °C / Inert atmosphere
16.2: (+)-CSA / 0.33 h / 50 °C
17.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 20 °C
18.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C / Inert atmosphere
18.2: 0.5 h / 20 °C / Inert atmosphere
19.1: 5,5-dimethyl-1,3-cyclohexadiene / 1.5 h / 110 °C / Inert atmosphere
20.1: tri-n-butyl-tin hydride; 1,1'-azobis(1-cyanocyclohexanenitrile) / 5,5-dimethyl-1,3-cyclohexadiene / 0.17 h / 180 °C / Inert atmosphere; Microwave irradiation
21.1: hydrogenchloride / water; methanol / 3.5 h / 30 °C
21.2: 1.5 h
22.1: hydrogenchloride / methanol; water / 3.5 h / 30 °C
22.2: 1.5 h
23.1: dmap; 2-azatricyclo[3.3.1.13,7]dec-2-yloxidanyl; [2,2]bipyridinyl; copper(l) chloride / acetonitrile / 0.5 h / 0 °C
24.1: dmap / tetrahydrofuran; toluene / 2 h / 0 °C
25.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 20 °C
26.1: L-Selectride / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere
27.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
27.2: 0.33 h / -20 °C / Inert atmosphere
28.1: dmap; 1,4-diaza-bicyclo[2.2.2]octane / acetonitrile / 76 h / 110 °C
29.1: N-Bromosuccinimide / tetrahydrofuran / 0.83 h / 0 °C
30.1: selenium(IV) oxide / tert-butyl alcohol / 80 °C
30.2: 0.42 h / 150 °C
30.3: 0.5 h / 0 - 20 °C
31.1: caesium carbonate / N,N-dimethyl-formamide / 5.67 h / 20 °C
31.2: 0.58 h / 0 °C
View Scheme
C21H24O6

C21H24O6

resiniferatoxin
57444-62-9

resiniferatoxin

Conditions
ConditionsYield
Multi-step reaction with 29 steps
1.1: triethylamine / dichloromethane / 0.75 h / 20 °C / Inert atmosphere
2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 °C
2.2: 0.42 h
3.1: lead(IV) tetraacetate; potassium carbonate / toluene / 1.17 h / 0 - 20 °C
4.1: triethylamine / dichloromethane / 1.25 h / 0 °C
5.1: dmap / toluene / 1.5 h / 20 °C / Darkness
6.1: sodium hydrogencarbonate / toluene / 0.5 h / 20 °C / Irradiation
7.1: potassium carbonate / methanol / 7.5 h / 0 °C
8.1: acetic anhydride; dimethyl sulfoxide / 2 h / 35 °C
9.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol / 0.17 h / -78 °C
10.1: 2,6-dimethylpyridine / water; dichloromethane / 0.5 h / 0 °C
11.1: 1,1'-azobis(1-cyanocyclohexanenitrile) / chlorobenzene / 0.5 h / Reflux; Inert atmosphere
12.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
13.1: triethylamine / dichloromethane / 1.5 h / 0 °C
14.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / hexane; dichloromethane / 0.5 h / 0 °C
15.1: diisobutylaluminium hydride / hexane; dichloromethane / 1 h / -93 °C / Inert atmosphere
15.2: (+)-CSA / 0.33 h / 50 °C
16.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 20 °C
17.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C / Inert atmosphere
17.2: 0.5 h / 20 °C / Inert atmosphere
18.1: 5,5-dimethyl-1,3-cyclohexadiene / 1.5 h / 110 °C / Inert atmosphere
19.1: tri-n-butyl-tin hydride; 1,1'-azobis(1-cyanocyclohexanenitrile) / 5,5-dimethyl-1,3-cyclohexadiene / 0.17 h / 180 °C / Inert atmosphere; Microwave irradiation
20.1: hydrogenchloride / water; methanol / 3.5 h / 30 °C
20.2: 1.5 h
21.1: dmap; 2-azatricyclo[3.3.1.13,7]dec-2-yloxidanyl; [2,2]bipyridinyl; copper(l) chloride / acetonitrile / 0.5 h / 0 °C
22.1: dmap / tetrahydrofuran; toluene / 2 h / 0 °C
23.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 20 °C
24.1: L-Selectride / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere
25.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
25.2: 0.33 h / -20 °C / Inert atmosphere
26.1: dmap; 1,4-diaza-bicyclo[2.2.2]octane / acetonitrile / 76 h / 110 °C
27.1: N-Bromosuccinimide / tetrahydrofuran / 0.83 h / 0 °C
28.1: selenium(IV) oxide / tert-butyl alcohol / 80 °C
28.2: 0.42 h / 150 °C
28.3: 0.5 h / 0 - 20 °C
29.1: caesium carbonate / N,N-dimethyl-formamide / 5.67 h / 20 °C
29.2: 0.58 h / 0 °C
View Scheme
Multi-step reaction with 30 steps
1.1: triethylamine / dichloromethane / 0.75 h / 20 °C / Inert atmosphere
2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 °C
2.2: 0.42 h
3.1: lead(IV) tetraacetate; potassium carbonate / toluene / 1.17 h / 0 - 20 °C
4.1: triethylamine / dichloromethane / 1.25 h / 0 °C
5.1: dmap / toluene / 1.5 h / 20 °C / Darkness
6.1: sodium hydrogencarbonate / toluene / 0.5 h / 20 °C / Irradiation
7.1: potassium carbonate / methanol / 7.5 h / 0 °C
8.1: acetic anhydride; dimethyl sulfoxide / 2 h / 35 °C
9.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol / 0.17 h / -78 °C
10.1: 2,6-dimethylpyridine / water; dichloromethane / 0.5 h / 0 °C
11.1: 1,1'-azobis(1-cyanocyclohexanenitrile) / chlorobenzene / 0.5 h / Reflux; Inert atmosphere
12.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
13.1: triethylamine / dichloromethane / 1.5 h / 0 °C
14.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / hexane; dichloromethane / 0.5 h / 0 °C
15.1: diisobutylaluminium hydride / hexane; dichloromethane / 1 h / -93 °C / Inert atmosphere
15.2: (+)-CSA / 0.33 h / 50 °C
16.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 20 °C
17.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C / Inert atmosphere
17.2: 0.5 h / 20 °C / Inert atmosphere
18.1: 5,5-dimethyl-1,3-cyclohexadiene / 1.5 h / 110 °C / Inert atmosphere
19.1: tri-n-butyl-tin hydride; 1,1'-azobis(1-cyanocyclohexanenitrile) / 5,5-dimethyl-1,3-cyclohexadiene / 0.17 h / 180 °C / Inert atmosphere; Microwave irradiation
20.1: hydrogenchloride / water; methanol / 3.5 h / 30 °C
20.2: 1.5 h
21.1: hydrogenchloride / methanol; water / 3.5 h / 30 °C
21.2: 1.5 h
22.1: dmap; 2-azatricyclo[3.3.1.13,7]dec-2-yloxidanyl; [2,2]bipyridinyl; copper(l) chloride / acetonitrile / 0.5 h / 0 °C
23.1: dmap / tetrahydrofuran; toluene / 2 h / 0 °C
24.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 20 °C
25.1: L-Selectride / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere
26.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
26.2: 0.33 h / -20 °C / Inert atmosphere
27.1: dmap; 1,4-diaza-bicyclo[2.2.2]octane / acetonitrile / 76 h / 110 °C
28.1: N-Bromosuccinimide / tetrahydrofuran / 0.83 h / 0 °C
29.1: selenium(IV) oxide / tert-butyl alcohol / 80 °C
29.2: 0.42 h / 150 °C
29.3: 0.5 h / 0 - 20 °C
30.1: caesium carbonate / N,N-dimethyl-formamide / 5.67 h / 20 °C
30.2: 0.58 h / 0 °C
View Scheme
C24H32O6Si

C24H32O6Si

resiniferatoxin
57444-62-9

resiniferatoxin

Conditions
ConditionsYield
Multi-step reaction with 28 steps
1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 °C
1.2: 0.42 h
2.1: lead(IV) tetraacetate; potassium carbonate / toluene / 1.17 h / 0 - 20 °C
3.1: triethylamine / dichloromethane / 1.25 h / 0 °C
4.1: dmap / toluene / 1.5 h / 20 °C / Darkness
5.1: sodium hydrogencarbonate / toluene / 0.5 h / 20 °C / Irradiation
6.1: potassium carbonate / methanol / 7.5 h / 0 °C
7.1: acetic anhydride; dimethyl sulfoxide / 2 h / 35 °C
8.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol / 0.17 h / -78 °C
9.1: 2,6-dimethylpyridine / water; dichloromethane / 0.5 h / 0 °C
10.1: 1,1'-azobis(1-cyanocyclohexanenitrile) / chlorobenzene / 0.5 h / Reflux; Inert atmosphere
11.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
12.1: triethylamine / dichloromethane / 1.5 h / 0 °C
13.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / hexane; dichloromethane / 0.5 h / 0 °C
14.1: diisobutylaluminium hydride / hexane; dichloromethane / 1 h / -93 °C / Inert atmosphere
14.2: (+)-CSA / 0.33 h / 50 °C
15.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 20 °C
16.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C / Inert atmosphere
16.2: 0.5 h / 20 °C / Inert atmosphere
17.1: 5,5-dimethyl-1,3-cyclohexadiene / 1.5 h / 110 °C / Inert atmosphere
18.1: tri-n-butyl-tin hydride; 1,1'-azobis(1-cyanocyclohexanenitrile) / 5,5-dimethyl-1,3-cyclohexadiene / 0.17 h / 180 °C / Inert atmosphere; Microwave irradiation
19.1: hydrogenchloride / water; methanol / 3.5 h / 30 °C
19.2: 1.5 h
20.1: dmap; 2-azatricyclo[3.3.1.13,7]dec-2-yloxidanyl; [2,2]bipyridinyl; copper(l) chloride / acetonitrile / 0.5 h / 0 °C
21.1: dmap / tetrahydrofuran; toluene / 2 h / 0 °C
22.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 20 °C
23.1: L-Selectride / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere
24.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
24.2: 0.33 h / -20 °C / Inert atmosphere
25.1: dmap; 1,4-diaza-bicyclo[2.2.2]octane / acetonitrile / 76 h / 110 °C
26.1: N-Bromosuccinimide / tetrahydrofuran / 0.83 h / 0 °C
27.1: selenium(IV) oxide / tert-butyl alcohol / 80 °C
27.2: 0.42 h / 150 °C
27.3: 0.5 h / 0 - 20 °C
28.1: caesium carbonate / N,N-dimethyl-formamide / 5.67 h / 20 °C
28.2: 0.58 h / 0 °C
View Scheme
Multi-step reaction with 29 steps
1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 °C
1.2: 0.42 h
2.1: lead(IV) tetraacetate; potassium carbonate / toluene / 1.17 h / 0 - 20 °C
3.1: triethylamine / dichloromethane / 1.25 h / 0 °C
4.1: dmap / toluene / 1.5 h / 20 °C / Darkness
5.1: sodium hydrogencarbonate / toluene / 0.5 h / 20 °C / Irradiation
6.1: potassium carbonate / methanol / 7.5 h / 0 °C
7.1: acetic anhydride; dimethyl sulfoxide / 2 h / 35 °C
8.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol / 0.17 h / -78 °C
9.1: 2,6-dimethylpyridine / water; dichloromethane / 0.5 h / 0 °C
10.1: 1,1'-azobis(1-cyanocyclohexanenitrile) / chlorobenzene / 0.5 h / Reflux; Inert atmosphere
11.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
12.1: triethylamine / dichloromethane / 1.5 h / 0 °C
13.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / hexane; dichloromethane / 0.5 h / 0 °C
14.1: diisobutylaluminium hydride / hexane; dichloromethane / 1 h / -93 °C / Inert atmosphere
14.2: (+)-CSA / 0.33 h / 50 °C
15.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 20 °C
16.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C / Inert atmosphere
16.2: 0.5 h / 20 °C / Inert atmosphere
17.1: 5,5-dimethyl-1,3-cyclohexadiene / 1.5 h / 110 °C / Inert atmosphere
18.1: tri-n-butyl-tin hydride; 1,1'-azobis(1-cyanocyclohexanenitrile) / 5,5-dimethyl-1,3-cyclohexadiene / 0.17 h / 180 °C / Inert atmosphere; Microwave irradiation
19.1: hydrogenchloride / water; methanol / 3.5 h / 30 °C
19.2: 1.5 h
20.1: hydrogenchloride / methanol; water / 3.5 h / 30 °C
20.2: 1.5 h
21.1: dmap; 2-azatricyclo[3.3.1.13,7]dec-2-yloxidanyl; [2,2]bipyridinyl; copper(l) chloride / acetonitrile / 0.5 h / 0 °C
22.1: dmap / tetrahydrofuran; toluene / 2 h / 0 °C
23.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 20 °C
24.1: L-Selectride / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere
25.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
25.2: 0.33 h / -20 °C / Inert atmosphere
26.1: dmap; 1,4-diaza-bicyclo[2.2.2]octane / acetonitrile / 76 h / 110 °C
27.1: N-Bromosuccinimide / tetrahydrofuran / 0.83 h / 0 °C
28.1: selenium(IV) oxide / tert-butyl alcohol / 80 °C
28.2: 0.42 h / 150 °C
28.3: 0.5 h / 0 - 20 °C
29.1: caesium carbonate / N,N-dimethyl-formamide / 5.67 h / 20 °C
29.2: 0.58 h / 0 °C
View Scheme
C15H9Cl3O3

C15H9Cl3O3

resiniferatoxin
57444-62-9

resiniferatoxin

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: dmap / tetrahydrofuran; toluene / 2 h / 0 °C
2.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 20 °C
3.1: L-Selectride / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere
4.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
4.2: 0.33 h / -20 °C / Inert atmosphere
5.1: dmap; 1,4-diaza-bicyclo[2.2.2]octane / acetonitrile / 76 h / 110 °C
6.1: N-Bromosuccinimide / tetrahydrofuran / 0.83 h / 0 °C
7.1: selenium(IV) oxide / tert-butyl alcohol / 80 °C
7.2: 0.42 h / 150 °C
7.3: 0.5 h / 0 - 20 °C
8.1: caesium carbonate / N,N-dimethyl-formamide / 5.67 h / 20 °C
8.2: 0.58 h / 0 °C
View Scheme
Homovanillic acid
306-08-1

Homovanillic acid

resiniferatoxin
57444-62-9

resiniferatoxin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 1H-imidazole / N,N-dimethyl-formamide / 3 h / 0 - 20 °C
2.1: acetic acid / tetrahydrofuran; water / 1 h / 0 °C
3.1: caesium carbonate / N,N-dimethyl-formamide / 5.67 h / 20 °C
3.2: 0.58 h / 0 °C
View Scheme
C29H38O8S4

C29H38O8S4

resiniferatoxin
57444-62-9

resiniferatoxin

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1.1: tri-n-butyl-tin hydride; 1,1'-azobis(1-cyanocyclohexanenitrile) / 5,5-dimethyl-1,3-cyclohexadiene / 0.17 h / 180 °C / Inert atmosphere; Microwave irradiation
2.1: hydrogenchloride / water; methanol / 3.5 h / 30 °C
2.2: 1.5 h
3.1: dmap; 2-azatricyclo[3.3.1.13,7]dec-2-yloxidanyl; [2,2]bipyridinyl; copper(l) chloride / acetonitrile / 0.5 h / 0 °C
4.1: dmap / tetrahydrofuran; toluene / 2 h / 0 °C
5.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 20 °C
6.1: L-Selectride / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere
7.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
7.2: 0.33 h / -20 °C / Inert atmosphere
8.1: dmap; 1,4-diaza-bicyclo[2.2.2]octane / acetonitrile / 76 h / 110 °C
9.1: N-Bromosuccinimide / tetrahydrofuran / 0.83 h / 0 °C
10.1: selenium(IV) oxide / tert-butyl alcohol / 80 °C
10.2: 0.42 h / 150 °C
10.3: 0.5 h / 0 - 20 °C
11.1: caesium carbonate / N,N-dimethyl-formamide / 5.67 h / 20 °C
11.2: 0.58 h / 0 °C
View Scheme
Multi-step reaction with 12 steps
1.1: tri-n-butyl-tin hydride; 1,1'-azobis(1-cyanocyclohexanenitrile) / 5,5-dimethyl-1,3-cyclohexadiene / 0.17 h / 180 °C / Inert atmosphere; Microwave irradiation
2.1: hydrogenchloride / water; methanol / 3.5 h / 30 °C
2.2: 1.5 h
3.1: hydrogenchloride / methanol; water / 3.5 h / 30 °C
3.2: 1.5 h
4.1: dmap; 2-azatricyclo[3.3.1.13,7]dec-2-yloxidanyl; [2,2]bipyridinyl; copper(l) chloride / acetonitrile / 0.5 h / 0 °C
5.1: dmap / tetrahydrofuran; toluene / 2 h / 0 °C
6.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 20 °C
7.1: L-Selectride / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere
8.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
8.2: 0.33 h / -20 °C / Inert atmosphere
9.1: dmap; 1,4-diaza-bicyclo[2.2.2]octane / acetonitrile / 76 h / 110 °C
10.1: N-Bromosuccinimide / tetrahydrofuran / 0.83 h / 0 °C
11.1: selenium(IV) oxide / tert-butyl alcohol / 80 °C
11.2: 0.42 h / 150 °C
11.3: 0.5 h / 0 - 20 °C
12.1: caesium carbonate / N,N-dimethyl-formamide / 5.67 h / 20 °C
12.2: 0.58 h / 0 °C
View Scheme
C21H24O7

C21H24O7

resiniferatoxin
57444-62-9

resiniferatoxin

Conditions
ConditionsYield
Multi-step reaction with 27 steps
1.1: lead(IV) tetraacetate; potassium carbonate / toluene / 1.17 h / 0 - 20 °C
2.1: triethylamine / dichloromethane / 1.25 h / 0 °C
3.1: dmap / toluene / 1.5 h / 20 °C / Darkness
4.1: sodium hydrogencarbonate / toluene / 0.5 h / 20 °C / Irradiation
5.1: potassium carbonate / methanol / 7.5 h / 0 °C
6.1: acetic anhydride; dimethyl sulfoxide / 2 h / 35 °C
7.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol / 0.17 h / -78 °C
8.1: 2,6-dimethylpyridine / water; dichloromethane / 0.5 h / 0 °C
9.1: 1,1'-azobis(1-cyanocyclohexanenitrile) / chlorobenzene / 0.5 h / Reflux; Inert atmosphere
10.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
11.1: triethylamine / dichloromethane / 1.5 h / 0 °C
12.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / hexane; dichloromethane / 0.5 h / 0 °C
13.1: diisobutylaluminium hydride / hexane; dichloromethane / 1 h / -93 °C / Inert atmosphere
13.2: (+)-CSA / 0.33 h / 50 °C
14.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 20 °C
15.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C / Inert atmosphere
15.2: 0.5 h / 20 °C / Inert atmosphere
16.1: 5,5-dimethyl-1,3-cyclohexadiene / 1.5 h / 110 °C / Inert atmosphere
17.1: tri-n-butyl-tin hydride; 1,1'-azobis(1-cyanocyclohexanenitrile) / 5,5-dimethyl-1,3-cyclohexadiene / 0.17 h / 180 °C / Inert atmosphere; Microwave irradiation
18.1: hydrogenchloride / water; methanol / 3.5 h / 30 °C
18.2: 1.5 h
19.1: dmap; 2-azatricyclo[3.3.1.13,7]dec-2-yloxidanyl; [2,2]bipyridinyl; copper(l) chloride / acetonitrile / 0.5 h / 0 °C
20.1: dmap / tetrahydrofuran; toluene / 2 h / 0 °C
21.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 20 °C
22.1: L-Selectride / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere
23.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
23.2: 0.33 h / -20 °C / Inert atmosphere
24.1: dmap; 1,4-diaza-bicyclo[2.2.2]octane / acetonitrile / 76 h / 110 °C
25.1: N-Bromosuccinimide / tetrahydrofuran / 0.83 h / 0 °C
26.1: selenium(IV) oxide / tert-butyl alcohol / 80 °C
26.2: 0.42 h / 150 °C
26.3: 0.5 h / 0 - 20 °C
27.1: caesium carbonate / N,N-dimethyl-formamide / 5.67 h / 20 °C
27.2: 0.58 h / 0 °C
View Scheme
Multi-step reaction with 28 steps
1.1: lead(IV) tetraacetate; potassium carbonate / toluene / 1.17 h / 0 - 20 °C
2.1: triethylamine / dichloromethane / 1.25 h / 0 °C
3.1: dmap / toluene / 1.5 h / 20 °C / Darkness
4.1: sodium hydrogencarbonate / toluene / 0.5 h / 20 °C / Irradiation
5.1: potassium carbonate / methanol / 7.5 h / 0 °C
6.1: acetic anhydride; dimethyl sulfoxide / 2 h / 35 °C
7.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol / 0.17 h / -78 °C
8.1: 2,6-dimethylpyridine / water; dichloromethane / 0.5 h / 0 °C
9.1: 1,1'-azobis(1-cyanocyclohexanenitrile) / chlorobenzene / 0.5 h / Reflux; Inert atmosphere
10.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
11.1: triethylamine / dichloromethane / 1.5 h / 0 °C
12.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / hexane; dichloromethane / 0.5 h / 0 °C
13.1: diisobutylaluminium hydride / hexane; dichloromethane / 1 h / -93 °C / Inert atmosphere
13.2: (+)-CSA / 0.33 h / 50 °C
14.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 20 °C
15.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C / Inert atmosphere
15.2: 0.5 h / 20 °C / Inert atmosphere
16.1: 5,5-dimethyl-1,3-cyclohexadiene / 1.5 h / 110 °C / Inert atmosphere
17.1: tri-n-butyl-tin hydride; 1,1'-azobis(1-cyanocyclohexanenitrile) / 5,5-dimethyl-1,3-cyclohexadiene / 0.17 h / 180 °C / Inert atmosphere; Microwave irradiation
18.1: hydrogenchloride / water; methanol / 3.5 h / 30 °C
18.2: 1.5 h
19.1: hydrogenchloride / methanol; water / 3.5 h / 30 °C
19.2: 1.5 h
20.1: dmap; 2-azatricyclo[3.3.1.13,7]dec-2-yloxidanyl; [2,2]bipyridinyl; copper(l) chloride / acetonitrile / 0.5 h / 0 °C
21.1: dmap / tetrahydrofuran; toluene / 2 h / 0 °C
22.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 20 °C
23.1: L-Selectride / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere
24.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
24.2: 0.33 h / -20 °C / Inert atmosphere
25.1: dmap; 1,4-diaza-bicyclo[2.2.2]octane / acetonitrile / 76 h / 110 °C
26.1: N-Bromosuccinimide / tetrahydrofuran / 0.83 h / 0 °C
27.1: selenium(IV) oxide / tert-butyl alcohol / 80 °C
27.2: 0.42 h / 150 °C
27.3: 0.5 h / 0 - 20 °C
28.1: caesium carbonate / N,N-dimethyl-formamide / 5.67 h / 20 °C
28.2: 0.58 h / 0 °C
View Scheme
C20H22O7

C20H22O7

resiniferatoxin
57444-62-9

resiniferatoxin

Conditions
ConditionsYield
Multi-step reaction with 26 steps
1.1: triethylamine / dichloromethane / 1.25 h / 0 °C
2.1: dmap / toluene / 1.5 h / 20 °C / Darkness
3.1: sodium hydrogencarbonate / toluene / 0.5 h / 20 °C / Irradiation
4.1: potassium carbonate / methanol / 7.5 h / 0 °C
5.1: acetic anhydride; dimethyl sulfoxide / 2 h / 35 °C
6.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol / 0.17 h / -78 °C
7.1: 2,6-dimethylpyridine / water; dichloromethane / 0.5 h / 0 °C
8.1: 1,1'-azobis(1-cyanocyclohexanenitrile) / chlorobenzene / 0.5 h / Reflux; Inert atmosphere
9.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
10.1: triethylamine / dichloromethane / 1.5 h / 0 °C
11.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / hexane; dichloromethane / 0.5 h / 0 °C
12.1: diisobutylaluminium hydride / hexane; dichloromethane / 1 h / -93 °C / Inert atmosphere
12.2: (+)-CSA / 0.33 h / 50 °C
13.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 20 °C
14.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C / Inert atmosphere
14.2: 0.5 h / 20 °C / Inert atmosphere
15.1: 5,5-dimethyl-1,3-cyclohexadiene / 1.5 h / 110 °C / Inert atmosphere
16.1: tri-n-butyl-tin hydride; 1,1'-azobis(1-cyanocyclohexanenitrile) / 5,5-dimethyl-1,3-cyclohexadiene / 0.17 h / 180 °C / Inert atmosphere; Microwave irradiation
17.1: hydrogenchloride / water; methanol / 3.5 h / 30 °C
17.2: 1.5 h
18.1: dmap; 2-azatricyclo[3.3.1.13,7]dec-2-yloxidanyl; [2,2]bipyridinyl; copper(l) chloride / acetonitrile / 0.5 h / 0 °C
19.1: dmap / tetrahydrofuran; toluene / 2 h / 0 °C
20.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 20 °C
21.1: L-Selectride / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere
22.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
22.2: 0.33 h / -20 °C / Inert atmosphere
23.1: dmap; 1,4-diaza-bicyclo[2.2.2]octane / acetonitrile / 76 h / 110 °C
24.1: N-Bromosuccinimide / tetrahydrofuran / 0.83 h / 0 °C
25.1: selenium(IV) oxide / tert-butyl alcohol / 80 °C
25.2: 0.42 h / 150 °C
25.3: 0.5 h / 0 - 20 °C
26.1: caesium carbonate / N,N-dimethyl-formamide / 5.67 h / 20 °C
26.2: 0.58 h / 0 °C
View Scheme
Multi-step reaction with 27 steps
1.1: triethylamine / dichloromethane / 1.25 h / 0 °C
2.1: dmap / toluene / 1.5 h / 20 °C / Darkness
3.1: sodium hydrogencarbonate / toluene / 0.5 h / 20 °C / Irradiation
4.1: potassium carbonate / methanol / 7.5 h / 0 °C
5.1: acetic anhydride; dimethyl sulfoxide / 2 h / 35 °C
6.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol / 0.17 h / -78 °C
7.1: 2,6-dimethylpyridine / water; dichloromethane / 0.5 h / 0 °C
8.1: 1,1'-azobis(1-cyanocyclohexanenitrile) / chlorobenzene / 0.5 h / Reflux; Inert atmosphere
9.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
10.1: triethylamine / dichloromethane / 1.5 h / 0 °C
11.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / hexane; dichloromethane / 0.5 h / 0 °C
12.1: diisobutylaluminium hydride / hexane; dichloromethane / 1 h / -93 °C / Inert atmosphere
12.2: (+)-CSA / 0.33 h / 50 °C
13.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 20 °C
14.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C / Inert atmosphere
14.2: 0.5 h / 20 °C / Inert atmosphere
15.1: 5,5-dimethyl-1,3-cyclohexadiene / 1.5 h / 110 °C / Inert atmosphere
16.1: tri-n-butyl-tin hydride; 1,1'-azobis(1-cyanocyclohexanenitrile) / 5,5-dimethyl-1,3-cyclohexadiene / 0.17 h / 180 °C / Inert atmosphere; Microwave irradiation
17.1: hydrogenchloride / water; methanol / 3.5 h / 30 °C
17.2: 1.5 h
18.1: hydrogenchloride / methanol; water / 3.5 h / 30 °C
18.2: 1.5 h
19.1: dmap; 2-azatricyclo[3.3.1.13,7]dec-2-yloxidanyl; [2,2]bipyridinyl; copper(l) chloride / acetonitrile / 0.5 h / 0 °C
20.1: dmap / tetrahydrofuran; toluene / 2 h / 0 °C
21.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 20 °C
22.1: L-Selectride / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere
23.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
23.2: 0.33 h / -20 °C / Inert atmosphere
24.1: dmap; 1,4-diaza-bicyclo[2.2.2]octane / acetonitrile / 76 h / 110 °C
25.1: N-Bromosuccinimide / tetrahydrofuran / 0.83 h / 0 °C
26.1: selenium(IV) oxide / tert-butyl alcohol / 80 °C
26.2: 0.42 h / 150 °C
26.3: 0.5 h / 0 - 20 °C
27.1: caesium carbonate / N,N-dimethyl-formamide / 5.67 h / 20 °C
27.2: 0.58 h / 0 °C
View Scheme
C21H24O9S

C21H24O9S

resiniferatoxin
57444-62-9

resiniferatoxin

Conditions
ConditionsYield
Multi-step reaction with 25 steps
1.1: dmap / toluene / 1.5 h / 20 °C / Darkness
2.1: sodium hydrogencarbonate / toluene / 0.5 h / 20 °C / Irradiation
3.1: potassium carbonate / methanol / 7.5 h / 0 °C
4.1: acetic anhydride; dimethyl sulfoxide / 2 h / 35 °C
5.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol / 0.17 h / -78 °C
6.1: 2,6-dimethylpyridine / water; dichloromethane / 0.5 h / 0 °C
7.1: 1,1'-azobis(1-cyanocyclohexanenitrile) / chlorobenzene / 0.5 h / Reflux; Inert atmosphere
8.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
9.1: triethylamine / dichloromethane / 1.5 h / 0 °C
10.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / hexane; dichloromethane / 0.5 h / 0 °C
11.1: diisobutylaluminium hydride / hexane; dichloromethane / 1 h / -93 °C / Inert atmosphere
11.2: (+)-CSA / 0.33 h / 50 °C
12.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 20 °C
13.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C / Inert atmosphere
13.2: 0.5 h / 20 °C / Inert atmosphere
14.1: 5,5-dimethyl-1,3-cyclohexadiene / 1.5 h / 110 °C / Inert atmosphere
15.1: tri-n-butyl-tin hydride; 1,1'-azobis(1-cyanocyclohexanenitrile) / 5,5-dimethyl-1,3-cyclohexadiene / 0.17 h / 180 °C / Inert atmosphere; Microwave irradiation
16.1: hydrogenchloride / water; methanol / 3.5 h / 30 °C
16.2: 1.5 h
17.1: dmap; 2-azatricyclo[3.3.1.13,7]dec-2-yloxidanyl; [2,2]bipyridinyl; copper(l) chloride / acetonitrile / 0.5 h / 0 °C
18.1: dmap / tetrahydrofuran; toluene / 2 h / 0 °C
19.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 20 °C
20.1: L-Selectride / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere
21.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
21.2: 0.33 h / -20 °C / Inert atmosphere
22.1: dmap; 1,4-diaza-bicyclo[2.2.2]octane / acetonitrile / 76 h / 110 °C
23.1: N-Bromosuccinimide / tetrahydrofuran / 0.83 h / 0 °C
24.1: selenium(IV) oxide / tert-butyl alcohol / 80 °C
24.2: 0.42 h / 150 °C
24.3: 0.5 h / 0 - 20 °C
25.1: caesium carbonate / N,N-dimethyl-formamide / 5.67 h / 20 °C
25.2: 0.58 h / 0 °C
View Scheme
Multi-step reaction with 26 steps
1.1: dmap / toluene / 1.5 h / 20 °C / Darkness
2.1: sodium hydrogencarbonate / toluene / 0.5 h / 20 °C / Irradiation
3.1: potassium carbonate / methanol / 7.5 h / 0 °C
4.1: acetic anhydride; dimethyl sulfoxide / 2 h / 35 °C
5.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol / 0.17 h / -78 °C
6.1: 2,6-dimethylpyridine / water; dichloromethane / 0.5 h / 0 °C
7.1: 1,1'-azobis(1-cyanocyclohexanenitrile) / chlorobenzene / 0.5 h / Reflux; Inert atmosphere
8.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
9.1: triethylamine / dichloromethane / 1.5 h / 0 °C
10.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / hexane; dichloromethane / 0.5 h / 0 °C
11.1: diisobutylaluminium hydride / hexane; dichloromethane / 1 h / -93 °C / Inert atmosphere
11.2: (+)-CSA / 0.33 h / 50 °C
12.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 20 °C
13.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C / Inert atmosphere
13.2: 0.5 h / 20 °C / Inert atmosphere
14.1: 5,5-dimethyl-1,3-cyclohexadiene / 1.5 h / 110 °C / Inert atmosphere
15.1: tri-n-butyl-tin hydride; 1,1'-azobis(1-cyanocyclohexanenitrile) / 5,5-dimethyl-1,3-cyclohexadiene / 0.17 h / 180 °C / Inert atmosphere; Microwave irradiation
16.1: hydrogenchloride / water; methanol / 3.5 h / 30 °C
16.2: 1.5 h
17.1: hydrogenchloride / methanol; water / 3.5 h / 30 °C
17.2: 1.5 h
18.1: dmap; 2-azatricyclo[3.3.1.13,7]dec-2-yloxidanyl; [2,2]bipyridinyl; copper(l) chloride / acetonitrile / 0.5 h / 0 °C
19.1: dmap / tetrahydrofuran; toluene / 2 h / 0 °C
20.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 20 °C
21.1: L-Selectride / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere
22.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
22.2: 0.33 h / -20 °C / Inert atmosphere
23.1: dmap; 1,4-diaza-bicyclo[2.2.2]octane / acetonitrile / 76 h / 110 °C
24.1: N-Bromosuccinimide / tetrahydrofuran / 0.83 h / 0 °C
25.1: selenium(IV) oxide / tert-butyl alcohol / 80 °C
25.2: 0.42 h / 150 °C
25.3: 0.5 h / 0 - 20 °C
26.1: caesium carbonate / N,N-dimethyl-formamide / 5.67 h / 20 °C
26.2: 0.58 h / 0 °C
View Scheme
C25H25NO7S

C25H25NO7S

resiniferatoxin
57444-62-9

resiniferatoxin

Conditions
ConditionsYield
Multi-step reaction with 24 steps
1.1: sodium hydrogencarbonate / toluene / 0.5 h / 20 °C / Irradiation
2.1: potassium carbonate / methanol / 7.5 h / 0 °C
3.1: acetic anhydride; dimethyl sulfoxide / 2 h / 35 °C
4.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol / 0.17 h / -78 °C
5.1: 2,6-dimethylpyridine / water; dichloromethane / 0.5 h / 0 °C
6.1: 1,1'-azobis(1-cyanocyclohexanenitrile) / chlorobenzene / 0.5 h / Reflux; Inert atmosphere
7.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
8.1: triethylamine / dichloromethane / 1.5 h / 0 °C
9.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / hexane; dichloromethane / 0.5 h / 0 °C
10.1: diisobutylaluminium hydride / hexane; dichloromethane / 1 h / -93 °C / Inert atmosphere
10.2: (+)-CSA / 0.33 h / 50 °C
11.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 20 °C
12.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C / Inert atmosphere
12.2: 0.5 h / 20 °C / Inert atmosphere
13.1: 5,5-dimethyl-1,3-cyclohexadiene / 1.5 h / 110 °C / Inert atmosphere
14.1: tri-n-butyl-tin hydride; 1,1'-azobis(1-cyanocyclohexanenitrile) / 5,5-dimethyl-1,3-cyclohexadiene / 0.17 h / 180 °C / Inert atmosphere; Microwave irradiation
15.1: hydrogenchloride / water; methanol / 3.5 h / 30 °C
15.2: 1.5 h
16.1: dmap; 2-azatricyclo[3.3.1.13,7]dec-2-yloxidanyl; [2,2]bipyridinyl; copper(l) chloride / acetonitrile / 0.5 h / 0 °C
17.1: dmap / tetrahydrofuran; toluene / 2 h / 0 °C
18.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 20 °C
19.1: L-Selectride / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere
20.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
20.2: 0.33 h / -20 °C / Inert atmosphere
21.1: dmap; 1,4-diaza-bicyclo[2.2.2]octane / acetonitrile / 76 h / 110 °C
22.1: N-Bromosuccinimide / tetrahydrofuran / 0.83 h / 0 °C
23.1: selenium(IV) oxide / tert-butyl alcohol / 80 °C
23.2: 0.42 h / 150 °C
23.3: 0.5 h / 0 - 20 °C
24.1: caesium carbonate / N,N-dimethyl-formamide / 5.67 h / 20 °C
24.2: 0.58 h / 0 °C
View Scheme
Multi-step reaction with 25 steps
1.1: sodium hydrogencarbonate / toluene / 0.5 h / 20 °C / Irradiation
2.1: potassium carbonate / methanol / 7.5 h / 0 °C
3.1: acetic anhydride; dimethyl sulfoxide / 2 h / 35 °C
4.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol / 0.17 h / -78 °C
5.1: 2,6-dimethylpyridine / water; dichloromethane / 0.5 h / 0 °C
6.1: 1,1'-azobis(1-cyanocyclohexanenitrile) / chlorobenzene / 0.5 h / Reflux; Inert atmosphere
7.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
8.1: triethylamine / dichloromethane / 1.5 h / 0 °C
9.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / hexane; dichloromethane / 0.5 h / 0 °C
10.1: diisobutylaluminium hydride / hexane; dichloromethane / 1 h / -93 °C / Inert atmosphere
10.2: (+)-CSA / 0.33 h / 50 °C
11.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 20 °C
12.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C / Inert atmosphere
12.2: 0.5 h / 20 °C / Inert atmosphere
13.1: 5,5-dimethyl-1,3-cyclohexadiene / 1.5 h / 110 °C / Inert atmosphere
14.1: tri-n-butyl-tin hydride; 1,1'-azobis(1-cyanocyclohexanenitrile) / 5,5-dimethyl-1,3-cyclohexadiene / 0.17 h / 180 °C / Inert atmosphere; Microwave irradiation
15.1: hydrogenchloride / water; methanol / 3.5 h / 30 °C
15.2: 1.5 h
16.1: hydrogenchloride / methanol; water / 3.5 h / 30 °C
16.2: 1.5 h
17.1: dmap; 2-azatricyclo[3.3.1.13,7]dec-2-yloxidanyl; [2,2]bipyridinyl; copper(l) chloride / acetonitrile / 0.5 h / 0 °C
18.1: dmap / tetrahydrofuran; toluene / 2 h / 0 °C
19.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 20 °C
20.1: L-Selectride / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere
21.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
21.2: 0.33 h / -20 °C / Inert atmosphere
22.1: dmap; 1,4-diaza-bicyclo[2.2.2]octane / acetonitrile / 76 h / 110 °C
23.1: N-Bromosuccinimide / tetrahydrofuran / 0.83 h / 0 °C
24.1: selenium(IV) oxide / tert-butyl alcohol / 80 °C
24.2: 0.42 h / 150 °C
24.3: 0.5 h / 0 - 20 °C
25.1: caesium carbonate / N,N-dimethyl-formamide / 5.67 h / 20 °C
25.2: 0.58 h / 0 °C
View Scheme
C26H26O6Se

C26H26O6Se

resiniferatoxin
57444-62-9

resiniferatoxin

Conditions
ConditionsYield
Multi-step reaction with 23 steps
1.1: potassium carbonate / methanol / 7.5 h / 0 °C
2.1: acetic anhydride; dimethyl sulfoxide / 2 h / 35 °C
3.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol / 0.17 h / -78 °C
4.1: 2,6-dimethylpyridine / water; dichloromethane / 0.5 h / 0 °C
5.1: 1,1'-azobis(1-cyanocyclohexanenitrile) / chlorobenzene / 0.5 h / Reflux; Inert atmosphere
6.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
7.1: triethylamine / dichloromethane / 1.5 h / 0 °C
8.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / hexane; dichloromethane / 0.5 h / 0 °C
9.1: diisobutylaluminium hydride / hexane; dichloromethane / 1 h / -93 °C / Inert atmosphere
9.2: (+)-CSA / 0.33 h / 50 °C
10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 20 °C
11.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C / Inert atmosphere
11.2: 0.5 h / 20 °C / Inert atmosphere
12.1: 5,5-dimethyl-1,3-cyclohexadiene / 1.5 h / 110 °C / Inert atmosphere
13.1: tri-n-butyl-tin hydride; 1,1'-azobis(1-cyanocyclohexanenitrile) / 5,5-dimethyl-1,3-cyclohexadiene / 0.17 h / 180 °C / Inert atmosphere; Microwave irradiation
14.1: hydrogenchloride / water; methanol / 3.5 h / 30 °C
14.2: 1.5 h
15.1: dmap; 2-azatricyclo[3.3.1.13,7]dec-2-yloxidanyl; [2,2]bipyridinyl; copper(l) chloride / acetonitrile / 0.5 h / 0 °C
16.1: dmap / tetrahydrofuran; toluene / 2 h / 0 °C
17.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 20 °C
18.1: L-Selectride / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere
19.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
19.2: 0.33 h / -20 °C / Inert atmosphere
20.1: dmap; 1,4-diaza-bicyclo[2.2.2]octane / acetonitrile / 76 h / 110 °C
21.1: N-Bromosuccinimide / tetrahydrofuran / 0.83 h / 0 °C
22.1: selenium(IV) oxide / tert-butyl alcohol / 80 °C
22.2: 0.42 h / 150 °C
22.3: 0.5 h / 0 - 20 °C
23.1: caesium carbonate / N,N-dimethyl-formamide / 5.67 h / 20 °C
23.2: 0.58 h / 0 °C
View Scheme
Multi-step reaction with 24 steps
1.1: potassium carbonate / methanol / 7.5 h / 0 °C
2.1: acetic anhydride; dimethyl sulfoxide / 2 h / 35 °C
3.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol / 0.17 h / -78 °C
4.1: 2,6-dimethylpyridine / water; dichloromethane / 0.5 h / 0 °C
5.1: 1,1'-azobis(1-cyanocyclohexanenitrile) / chlorobenzene / 0.5 h / Reflux; Inert atmosphere
6.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
7.1: triethylamine / dichloromethane / 1.5 h / 0 °C
8.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / hexane; dichloromethane / 0.5 h / 0 °C
9.1: diisobutylaluminium hydride / hexane; dichloromethane / 1 h / -93 °C / Inert atmosphere
9.2: (+)-CSA / 0.33 h / 50 °C
10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 20 °C
11.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C / Inert atmosphere
11.2: 0.5 h / 20 °C / Inert atmosphere
12.1: 5,5-dimethyl-1,3-cyclohexadiene / 1.5 h / 110 °C / Inert atmosphere
13.1: tri-n-butyl-tin hydride; 1,1'-azobis(1-cyanocyclohexanenitrile) / 5,5-dimethyl-1,3-cyclohexadiene / 0.17 h / 180 °C / Inert atmosphere; Microwave irradiation
14.1: hydrogenchloride / water; methanol / 3.5 h / 30 °C
14.2: 1.5 h
15.1: hydrogenchloride / methanol; water / 3.5 h / 30 °C
15.2: 1.5 h
16.1: dmap; 2-azatricyclo[3.3.1.13,7]dec-2-yloxidanyl; [2,2]bipyridinyl; copper(l) chloride / acetonitrile / 0.5 h / 0 °C
17.1: dmap / tetrahydrofuran; toluene / 2 h / 0 °C
18.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 20 °C
19.1: L-Selectride / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere
20.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
20.2: 0.33 h / -20 °C / Inert atmosphere
21.1: dmap; 1,4-diaza-bicyclo[2.2.2]octane / acetonitrile / 76 h / 110 °C
22.1: N-Bromosuccinimide / tetrahydrofuran / 0.83 h / 0 °C
23.1: selenium(IV) oxide / tert-butyl alcohol / 80 °C
23.2: 0.42 h / 150 °C
23.3: 0.5 h / 0 - 20 °C
24.1: caesium carbonate / N,N-dimethyl-formamide / 5.67 h / 20 °C
24.2: 0.58 h / 0 °C
View Scheme
C19H22O5Se

C19H22O5Se

resiniferatoxin
57444-62-9

resiniferatoxin

Conditions
ConditionsYield
Multi-step reaction with 22 steps
1.1: acetic anhydride; dimethyl sulfoxide / 2 h / 35 °C
2.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol / 0.17 h / -78 °C
3.1: 2,6-dimethylpyridine / water; dichloromethane / 0.5 h / 0 °C
4.1: 1,1'-azobis(1-cyanocyclohexanenitrile) / chlorobenzene / 0.5 h / Reflux; Inert atmosphere
5.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
6.1: triethylamine / dichloromethane / 1.5 h / 0 °C
7.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / hexane; dichloromethane / 0.5 h / 0 °C
8.1: diisobutylaluminium hydride / hexane; dichloromethane / 1 h / -93 °C / Inert atmosphere
8.2: (+)-CSA / 0.33 h / 50 °C
9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 20 °C
10.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C / Inert atmosphere
10.2: 0.5 h / 20 °C / Inert atmosphere
11.1: 5,5-dimethyl-1,3-cyclohexadiene / 1.5 h / 110 °C / Inert atmosphere
12.1: tri-n-butyl-tin hydride; 1,1'-azobis(1-cyanocyclohexanenitrile) / 5,5-dimethyl-1,3-cyclohexadiene / 0.17 h / 180 °C / Inert atmosphere; Microwave irradiation
13.1: hydrogenchloride / water; methanol / 3.5 h / 30 °C
13.2: 1.5 h
14.1: dmap; 2-azatricyclo[3.3.1.13,7]dec-2-yloxidanyl; [2,2]bipyridinyl; copper(l) chloride / acetonitrile / 0.5 h / 0 °C
15.1: dmap / tetrahydrofuran; toluene / 2 h / 0 °C
16.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 20 °C
17.1: L-Selectride / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere
18.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
18.2: 0.33 h / -20 °C / Inert atmosphere
19.1: dmap; 1,4-diaza-bicyclo[2.2.2]octane / acetonitrile / 76 h / 110 °C
20.1: N-Bromosuccinimide / tetrahydrofuran / 0.83 h / 0 °C
21.1: selenium(IV) oxide / tert-butyl alcohol / 80 °C
21.2: 0.42 h / 150 °C
21.3: 0.5 h / 0 - 20 °C
22.1: caesium carbonate / N,N-dimethyl-formamide / 5.67 h / 20 °C
22.2: 0.58 h / 0 °C
View Scheme
Multi-step reaction with 23 steps
1.1: acetic anhydride; dimethyl sulfoxide / 2 h / 35 °C
2.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol / 0.17 h / -78 °C
3.1: 2,6-dimethylpyridine / water; dichloromethane / 0.5 h / 0 °C
4.1: 1,1'-azobis(1-cyanocyclohexanenitrile) / chlorobenzene / 0.5 h / Reflux; Inert atmosphere
5.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
6.1: triethylamine / dichloromethane / 1.5 h / 0 °C
7.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / hexane; dichloromethane / 0.5 h / 0 °C
8.1: diisobutylaluminium hydride / hexane; dichloromethane / 1 h / -93 °C / Inert atmosphere
8.2: (+)-CSA / 0.33 h / 50 °C
9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 20 °C
10.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C / Inert atmosphere
10.2: 0.5 h / 20 °C / Inert atmosphere
11.1: 5,5-dimethyl-1,3-cyclohexadiene / 1.5 h / 110 °C / Inert atmosphere
12.1: tri-n-butyl-tin hydride; 1,1'-azobis(1-cyanocyclohexanenitrile) / 5,5-dimethyl-1,3-cyclohexadiene / 0.17 h / 180 °C / Inert atmosphere; Microwave irradiation
13.1: hydrogenchloride / water; methanol / 3.5 h / 30 °C
13.2: 1.5 h
14.1: hydrogenchloride / methanol; water / 3.5 h / 30 °C
14.2: 1.5 h
15.1: dmap; 2-azatricyclo[3.3.1.13,7]dec-2-yloxidanyl; [2,2]bipyridinyl; copper(l) chloride / acetonitrile / 0.5 h / 0 °C
16.1: dmap / tetrahydrofuran; toluene / 2 h / 0 °C
17.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 20 °C
18.1: L-Selectride / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere
19.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
19.2: 0.33 h / -20 °C / Inert atmosphere
20.1: dmap; 1,4-diaza-bicyclo[2.2.2]octane / acetonitrile / 76 h / 110 °C
21.1: N-Bromosuccinimide / tetrahydrofuran / 0.83 h / 0 °C
22.1: selenium(IV) oxide / tert-butyl alcohol / 80 °C
22.2: 0.42 h / 150 °C
22.3: 0.5 h / 0 - 20 °C
23.1: caesium carbonate / N,N-dimethyl-formamide / 5.67 h / 20 °C
23.2: 0.58 h / 0 °C
View Scheme
C19H20O5Se

C19H20O5Se

resiniferatoxin
57444-62-9

resiniferatoxin

Conditions
ConditionsYield
Multi-step reaction with 21 steps
1.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol / 0.17 h / -78 °C
2.1: 2,6-dimethylpyridine / water; dichloromethane / 0.5 h / 0 °C
3.1: 1,1'-azobis(1-cyanocyclohexanenitrile) / chlorobenzene / 0.5 h / Reflux; Inert atmosphere
4.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
5.1: triethylamine / dichloromethane / 1.5 h / 0 °C
6.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / hexane; dichloromethane / 0.5 h / 0 °C
7.1: diisobutylaluminium hydride / hexane; dichloromethane / 1 h / -93 °C / Inert atmosphere
7.2: (+)-CSA / 0.33 h / 50 °C
8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 20 °C
9.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C / Inert atmosphere
9.2: 0.5 h / 20 °C / Inert atmosphere
10.1: 5,5-dimethyl-1,3-cyclohexadiene / 1.5 h / 110 °C / Inert atmosphere
11.1: tri-n-butyl-tin hydride; 1,1'-azobis(1-cyanocyclohexanenitrile) / 5,5-dimethyl-1,3-cyclohexadiene / 0.17 h / 180 °C / Inert atmosphere; Microwave irradiation
12.1: hydrogenchloride / water; methanol / 3.5 h / 30 °C
12.2: 1.5 h
13.1: dmap; 2-azatricyclo[3.3.1.13,7]dec-2-yloxidanyl; [2,2]bipyridinyl; copper(l) chloride / acetonitrile / 0.5 h / 0 °C
14.1: dmap / tetrahydrofuran; toluene / 2 h / 0 °C
15.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 20 °C
16.1: L-Selectride / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere
17.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
17.2: 0.33 h / -20 °C / Inert atmosphere
18.1: dmap; 1,4-diaza-bicyclo[2.2.2]octane / acetonitrile / 76 h / 110 °C
19.1: N-Bromosuccinimide / tetrahydrofuran / 0.83 h / 0 °C
20.1: selenium(IV) oxide / tert-butyl alcohol / 80 °C
20.2: 0.42 h / 150 °C
20.3: 0.5 h / 0 - 20 °C
21.1: caesium carbonate / N,N-dimethyl-formamide / 5.67 h / 20 °C
21.2: 0.58 h / 0 °C
View Scheme
Multi-step reaction with 22 steps
1.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol / 0.17 h / -78 °C
2.1: 2,6-dimethylpyridine / water; dichloromethane / 0.5 h / 0 °C
3.1: 1,1'-azobis(1-cyanocyclohexanenitrile) / chlorobenzene / 0.5 h / Reflux; Inert atmosphere
4.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
5.1: triethylamine / dichloromethane / 1.5 h / 0 °C
6.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / hexane; dichloromethane / 0.5 h / 0 °C
7.1: diisobutylaluminium hydride / hexane; dichloromethane / 1 h / -93 °C / Inert atmosphere
7.2: (+)-CSA / 0.33 h / 50 °C
8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 20 °C
9.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C / Inert atmosphere
9.2: 0.5 h / 20 °C / Inert atmosphere
10.1: 5,5-dimethyl-1,3-cyclohexadiene / 1.5 h / 110 °C / Inert atmosphere
11.1: tri-n-butyl-tin hydride; 1,1'-azobis(1-cyanocyclohexanenitrile) / 5,5-dimethyl-1,3-cyclohexadiene / 0.17 h / 180 °C / Inert atmosphere; Microwave irradiation
12.1: hydrogenchloride / water; methanol / 3.5 h / 30 °C
12.2: 1.5 h
13.1: hydrogenchloride / methanol; water / 3.5 h / 30 °C
13.2: 1.5 h
14.1: dmap; 2-azatricyclo[3.3.1.13,7]dec-2-yloxidanyl; [2,2]bipyridinyl; copper(l) chloride / acetonitrile / 0.5 h / 0 °C
15.1: dmap / tetrahydrofuran; toluene / 2 h / 0 °C
16.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 20 °C
17.1: L-Selectride / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere
18.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
18.2: 0.33 h / -20 °C / Inert atmosphere
19.1: dmap; 1,4-diaza-bicyclo[2.2.2]octane / acetonitrile / 76 h / 110 °C
20.1: N-Bromosuccinimide / tetrahydrofuran / 0.83 h / 0 °C
21.1: selenium(IV) oxide / tert-butyl alcohol / 80 °C
21.2: 0.42 h / 150 °C
21.3: 0.5 h / 0 - 20 °C
22.1: caesium carbonate / N,N-dimethyl-formamide / 5.67 h / 20 °C
22.2: 0.58 h / 0 °C
View Scheme
C19H22O5Se

C19H22O5Se

resiniferatoxin
57444-62-9

resiniferatoxin

Conditions
ConditionsYield
Multi-step reaction with 20 steps
1.1: 2,6-dimethylpyridine / water; dichloromethane / 0.5 h / 0 °C
2.1: 1,1'-azobis(1-cyanocyclohexanenitrile) / chlorobenzene / 0.5 h / Reflux; Inert atmosphere
3.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
4.1: triethylamine / dichloromethane / 1.5 h / 0 °C
5.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / hexane; dichloromethane / 0.5 h / 0 °C
6.1: diisobutylaluminium hydride / hexane; dichloromethane / 1 h / -93 °C / Inert atmosphere
6.2: (+)-CSA / 0.33 h / 50 °C
7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 20 °C
8.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C / Inert atmosphere
8.2: 0.5 h / 20 °C / Inert atmosphere
9.1: 5,5-dimethyl-1,3-cyclohexadiene / 1.5 h / 110 °C / Inert atmosphere
10.1: tri-n-butyl-tin hydride; 1,1'-azobis(1-cyanocyclohexanenitrile) / 5,5-dimethyl-1,3-cyclohexadiene / 0.17 h / 180 °C / Inert atmosphere; Microwave irradiation
11.1: hydrogenchloride / water; methanol / 3.5 h / 30 °C
11.2: 1.5 h
12.1: dmap; 2-azatricyclo[3.3.1.13,7]dec-2-yloxidanyl; [2,2]bipyridinyl; copper(l) chloride / acetonitrile / 0.5 h / 0 °C
13.1: dmap / tetrahydrofuran; toluene / 2 h / 0 °C
14.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 20 °C
15.1: L-Selectride / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere
16.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
16.2: 0.33 h / -20 °C / Inert atmosphere
17.1: dmap; 1,4-diaza-bicyclo[2.2.2]octane / acetonitrile / 76 h / 110 °C
18.1: N-Bromosuccinimide / tetrahydrofuran / 0.83 h / 0 °C
19.1: selenium(IV) oxide / tert-butyl alcohol / 80 °C
19.2: 0.42 h / 150 °C
19.3: 0.5 h / 0 - 20 °C
20.1: caesium carbonate / N,N-dimethyl-formamide / 5.67 h / 20 °C
20.2: 0.58 h / 0 °C
View Scheme
Multi-step reaction with 21 steps
1.1: 2,6-dimethylpyridine / water; dichloromethane / 0.5 h / 0 °C
2.1: 1,1'-azobis(1-cyanocyclohexanenitrile) / chlorobenzene / 0.5 h / Reflux; Inert atmosphere
3.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
4.1: triethylamine / dichloromethane / 1.5 h / 0 °C
5.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / hexane; dichloromethane / 0.5 h / 0 °C
6.1: diisobutylaluminium hydride / hexane; dichloromethane / 1 h / -93 °C / Inert atmosphere
6.2: (+)-CSA / 0.33 h / 50 °C
7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 20 °C
8.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C / Inert atmosphere
8.2: 0.5 h / 20 °C / Inert atmosphere
9.1: 5,5-dimethyl-1,3-cyclohexadiene / 1.5 h / 110 °C / Inert atmosphere
10.1: tri-n-butyl-tin hydride; 1,1'-azobis(1-cyanocyclohexanenitrile) / 5,5-dimethyl-1,3-cyclohexadiene / 0.17 h / 180 °C / Inert atmosphere; Microwave irradiation
11.1: hydrogenchloride / water; methanol / 3.5 h / 30 °C
11.2: 1.5 h
12.1: hydrogenchloride / methanol; water / 3.5 h / 30 °C
12.2: 1.5 h
13.1: dmap; 2-azatricyclo[3.3.1.13,7]dec-2-yloxidanyl; [2,2]bipyridinyl; copper(l) chloride / acetonitrile / 0.5 h / 0 °C
14.1: dmap / tetrahydrofuran; toluene / 2 h / 0 °C
15.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 20 °C
16.1: L-Selectride / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere
17.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
17.2: 0.33 h / -20 °C / Inert atmosphere
18.1: dmap; 1,4-diaza-bicyclo[2.2.2]octane / acetonitrile / 76 h / 110 °C
19.1: N-Bromosuccinimide / tetrahydrofuran / 0.83 h / 0 °C
20.1: selenium(IV) oxide / tert-butyl alcohol / 80 °C
20.2: 0.42 h / 150 °C
20.3: 0.5 h / 0 - 20 °C
21.1: caesium carbonate / N,N-dimethyl-formamide / 5.67 h / 20 °C
21.2: 0.58 h / 0 °C
View Scheme
C22H30O5SeSi

C22H30O5SeSi

resiniferatoxin
57444-62-9

resiniferatoxin

Conditions
ConditionsYield
Multi-step reaction with 19 steps
1.1: 1,1'-azobis(1-cyanocyclohexanenitrile) / chlorobenzene / 0.5 h / Reflux; Inert atmosphere
2.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
3.1: triethylamine / dichloromethane / 1.5 h / 0 °C
4.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / hexane; dichloromethane / 0.5 h / 0 °C
5.1: diisobutylaluminium hydride / hexane; dichloromethane / 1 h / -93 °C / Inert atmosphere
5.2: (+)-CSA / 0.33 h / 50 °C
6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 20 °C
7.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C / Inert atmosphere
7.2: 0.5 h / 20 °C / Inert atmosphere
8.1: 5,5-dimethyl-1,3-cyclohexadiene / 1.5 h / 110 °C / Inert atmosphere
9.1: tri-n-butyl-tin hydride; 1,1'-azobis(1-cyanocyclohexanenitrile) / 5,5-dimethyl-1,3-cyclohexadiene / 0.17 h / 180 °C / Inert atmosphere; Microwave irradiation
10.1: hydrogenchloride / water; methanol / 3.5 h / 30 °C
10.2: 1.5 h
11.1: dmap; 2-azatricyclo[3.3.1.13,7]dec-2-yloxidanyl; [2,2]bipyridinyl; copper(l) chloride / acetonitrile / 0.5 h / 0 °C
12.1: dmap / tetrahydrofuran; toluene / 2 h / 0 °C
13.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 20 °C
14.1: L-Selectride / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere
15.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
15.2: 0.33 h / -20 °C / Inert atmosphere
16.1: dmap; 1,4-diaza-bicyclo[2.2.2]octane / acetonitrile / 76 h / 110 °C
17.1: N-Bromosuccinimide / tetrahydrofuran / 0.83 h / 0 °C
18.1: selenium(IV) oxide / tert-butyl alcohol / 80 °C
18.2: 0.42 h / 150 °C
18.3: 0.5 h / 0 - 20 °C
19.1: caesium carbonate / N,N-dimethyl-formamide / 5.67 h / 20 °C
19.2: 0.58 h / 0 °C
View Scheme
Multi-step reaction with 20 steps
1.1: 1,1'-azobis(1-cyanocyclohexanenitrile) / chlorobenzene / 0.5 h / Reflux; Inert atmosphere
2.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
3.1: triethylamine / dichloromethane / 1.5 h / 0 °C
4.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / hexane; dichloromethane / 0.5 h / 0 °C
5.1: diisobutylaluminium hydride / hexane; dichloromethane / 1 h / -93 °C / Inert atmosphere
5.2: (+)-CSA / 0.33 h / 50 °C
6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 20 °C
7.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C / Inert atmosphere
7.2: 0.5 h / 20 °C / Inert atmosphere
8.1: 5,5-dimethyl-1,3-cyclohexadiene / 1.5 h / 110 °C / Inert atmosphere
9.1: tri-n-butyl-tin hydride; 1,1'-azobis(1-cyanocyclohexanenitrile) / 5,5-dimethyl-1,3-cyclohexadiene / 0.17 h / 180 °C / Inert atmosphere; Microwave irradiation
10.1: hydrogenchloride / water; methanol / 3.5 h / 30 °C
10.2: 1.5 h
11.1: hydrogenchloride / methanol; water / 3.5 h / 30 °C
11.2: 1.5 h
12.1: dmap; 2-azatricyclo[3.3.1.13,7]dec-2-yloxidanyl; [2,2]bipyridinyl; copper(l) chloride / acetonitrile / 0.5 h / 0 °C
13.1: dmap / tetrahydrofuran; toluene / 2 h / 0 °C
14.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 20 °C
15.1: L-Selectride / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere
16.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
16.2: 0.33 h / -20 °C / Inert atmosphere
17.1: dmap; 1,4-diaza-bicyclo[2.2.2]octane / acetonitrile / 76 h / 110 °C
18.1: N-Bromosuccinimide / tetrahydrofuran / 0.83 h / 0 °C
19.1: selenium(IV) oxide / tert-butyl alcohol / 80 °C
19.2: 0.42 h / 150 °C
19.3: 0.5 h / 0 - 20 °C
20.1: caesium carbonate / N,N-dimethyl-formamide / 5.67 h / 20 °C
20.2: 0.58 h / 0 °C
View Scheme
C46H70O7Si3

C46H70O7Si3

resiniferatoxin
57444-62-9

resiniferatoxin

Conditions
ConditionsYield
Multi-step reaction with 18 steps
1.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
2.1: triethylamine / dichloromethane / 1.5 h / 0 °C
3.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / hexane; dichloromethane / 0.5 h / 0 °C
4.1: diisobutylaluminium hydride / hexane; dichloromethane / 1 h / -93 °C / Inert atmosphere
4.2: (+)-CSA / 0.33 h / 50 °C
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 20 °C
6.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C / Inert atmosphere
6.2: 0.5 h / 20 °C / Inert atmosphere
7.1: 5,5-dimethyl-1,3-cyclohexadiene / 1.5 h / 110 °C / Inert atmosphere
8.1: tri-n-butyl-tin hydride; 1,1'-azobis(1-cyanocyclohexanenitrile) / 5,5-dimethyl-1,3-cyclohexadiene / 0.17 h / 180 °C / Inert atmosphere; Microwave irradiation
9.1: hydrogenchloride / water; methanol / 3.5 h / 30 °C
9.2: 1.5 h
10.1: dmap; 2-azatricyclo[3.3.1.13,7]dec-2-yloxidanyl; [2,2]bipyridinyl; copper(l) chloride / acetonitrile / 0.5 h / 0 °C
11.1: dmap / tetrahydrofuran; toluene / 2 h / 0 °C
12.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 20 °C
13.1: L-Selectride / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere
14.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
14.2: 0.33 h / -20 °C / Inert atmosphere
15.1: dmap; 1,4-diaza-bicyclo[2.2.2]octane / acetonitrile / 76 h / 110 °C
16.1: N-Bromosuccinimide / tetrahydrofuran / 0.83 h / 0 °C
17.1: selenium(IV) oxide / tert-butyl alcohol / 80 °C
17.2: 0.42 h / 150 °C
17.3: 0.5 h / 0 - 20 °C
18.1: caesium carbonate / N,N-dimethyl-formamide / 5.67 h / 20 °C
18.2: 0.58 h / 0 °C
View Scheme
Multi-step reaction with 19 steps
1.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
2.1: triethylamine / dichloromethane / 1.5 h / 0 °C
3.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / hexane; dichloromethane / 0.5 h / 0 °C
4.1: diisobutylaluminium hydride / hexane; dichloromethane / 1 h / -93 °C / Inert atmosphere
4.2: (+)-CSA / 0.33 h / 50 °C
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 20 °C
6.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C / Inert atmosphere
6.2: 0.5 h / 20 °C / Inert atmosphere
7.1: 5,5-dimethyl-1,3-cyclohexadiene / 1.5 h / 110 °C / Inert atmosphere
8.1: tri-n-butyl-tin hydride; 1,1'-azobis(1-cyanocyclohexanenitrile) / 5,5-dimethyl-1,3-cyclohexadiene / 0.17 h / 180 °C / Inert atmosphere; Microwave irradiation
9.1: hydrogenchloride / water; methanol / 3.5 h / 30 °C
9.2: 1.5 h
10.1: hydrogenchloride / methanol; water / 3.5 h / 30 °C
10.2: 1.5 h
11.1: dmap; 2-azatricyclo[3.3.1.13,7]dec-2-yloxidanyl; [2,2]bipyridinyl; copper(l) chloride / acetonitrile / 0.5 h / 0 °C
12.1: dmap / tetrahydrofuran; toluene / 2 h / 0 °C
13.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 20 °C
14.1: L-Selectride / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere
15.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
15.2: 0.33 h / -20 °C / Inert atmosphere
16.1: dmap; 1,4-diaza-bicyclo[2.2.2]octane / acetonitrile / 76 h / 110 °C
17.1: N-Bromosuccinimide / tetrahydrofuran / 0.83 h / 0 °C
18.1: selenium(IV) oxide / tert-butyl alcohol / 80 °C
18.2: 0.42 h / 150 °C
18.3: 0.5 h / 0 - 20 °C
19.1: caesium carbonate / N,N-dimethyl-formamide / 5.67 h / 20 °C
19.2: 0.58 h / 0 °C
View Scheme
C40H54O6Si2

C40H54O6Si2

resiniferatoxin
57444-62-9

resiniferatoxin

Conditions
ConditionsYield
Multi-step reaction with 17 steps
1.1: triethylamine / dichloromethane / 1.5 h / 0 °C
2.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / hexane; dichloromethane / 0.5 h / 0 °C
3.1: diisobutylaluminium hydride / hexane; dichloromethane / 1 h / -93 °C / Inert atmosphere
3.2: (+)-CSA / 0.33 h / 50 °C
4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 20 °C
5.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C / Inert atmosphere
5.2: 0.5 h / 20 °C / Inert atmosphere
6.1: 5,5-dimethyl-1,3-cyclohexadiene / 1.5 h / 110 °C / Inert atmosphere
7.1: tri-n-butyl-tin hydride; 1,1'-azobis(1-cyanocyclohexanenitrile) / 5,5-dimethyl-1,3-cyclohexadiene / 0.17 h / 180 °C / Inert atmosphere; Microwave irradiation
8.1: hydrogenchloride / water; methanol / 3.5 h / 30 °C
8.2: 1.5 h
9.1: dmap; 2-azatricyclo[3.3.1.13,7]dec-2-yloxidanyl; [2,2]bipyridinyl; copper(l) chloride / acetonitrile / 0.5 h / 0 °C
10.1: dmap / tetrahydrofuran; toluene / 2 h / 0 °C
11.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 20 °C
12.1: L-Selectride / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere
13.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
13.2: 0.33 h / -20 °C / Inert atmosphere
14.1: dmap; 1,4-diaza-bicyclo[2.2.2]octane / acetonitrile / 76 h / 110 °C
15.1: N-Bromosuccinimide / tetrahydrofuran / 0.83 h / 0 °C
16.1: selenium(IV) oxide / tert-butyl alcohol / 80 °C
16.2: 0.42 h / 150 °C
16.3: 0.5 h / 0 - 20 °C
17.1: caesium carbonate / N,N-dimethyl-formamide / 5.67 h / 20 °C
17.2: 0.58 h / 0 °C
View Scheme
Multi-step reaction with 18 steps
1.1: triethylamine / dichloromethane / 1.5 h / 0 °C
2.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / hexane; dichloromethane / 0.5 h / 0 °C
3.1: diisobutylaluminium hydride / hexane; dichloromethane / 1 h / -93 °C / Inert atmosphere
3.2: (+)-CSA / 0.33 h / 50 °C
4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 20 °C
5.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C / Inert atmosphere
5.2: 0.5 h / 20 °C / Inert atmosphere
6.1: 5,5-dimethyl-1,3-cyclohexadiene / 1.5 h / 110 °C / Inert atmosphere
7.1: tri-n-butyl-tin hydride; 1,1'-azobis(1-cyanocyclohexanenitrile) / 5,5-dimethyl-1,3-cyclohexadiene / 0.17 h / 180 °C / Inert atmosphere; Microwave irradiation
8.1: hydrogenchloride / water; methanol / 3.5 h / 30 °C
8.2: 1.5 h
9.1: hydrogenchloride / methanol; water / 3.5 h / 30 °C
9.2: 1.5 h
10.1: dmap; 2-azatricyclo[3.3.1.13,7]dec-2-yloxidanyl; [2,2]bipyridinyl; copper(l) chloride / acetonitrile / 0.5 h / 0 °C
11.1: dmap / tetrahydrofuran; toluene / 2 h / 0 °C
12.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 20 °C
13.1: L-Selectride / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere
14.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
14.2: 0.33 h / -20 °C / Inert atmosphere
15.1: dmap; 1,4-diaza-bicyclo[2.2.2]octane / acetonitrile / 76 h / 110 °C
16.1: N-Bromosuccinimide / tetrahydrofuran / 0.83 h / 0 °C
17.1: selenium(IV) oxide / tert-butyl alcohol / 80 °C
17.2: 0.42 h / 150 °C
17.3: 0.5 h / 0 - 20 °C
18.1: caesium carbonate / N,N-dimethyl-formamide / 5.67 h / 20 °C
18.2: 0.58 h / 0 °C
View Scheme
C46H68O6Si3

C46H68O6Si3

resiniferatoxin
57444-62-9

resiniferatoxin

Conditions
ConditionsYield
Multi-step reaction with 16 steps
1.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / hexane; dichloromethane / 0.5 h / 0 °C
2.1: diisobutylaluminium hydride / hexane; dichloromethane / 1 h / -93 °C / Inert atmosphere
2.2: (+)-CSA / 0.33 h / 50 °C
3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 20 °C
4.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C / Inert atmosphere
4.2: 0.5 h / 20 °C / Inert atmosphere
5.1: 5,5-dimethyl-1,3-cyclohexadiene / 1.5 h / 110 °C / Inert atmosphere
6.1: tri-n-butyl-tin hydride; 1,1'-azobis(1-cyanocyclohexanenitrile) / 5,5-dimethyl-1,3-cyclohexadiene / 0.17 h / 180 °C / Inert atmosphere; Microwave irradiation
7.1: hydrogenchloride / water; methanol / 3.5 h / 30 °C
7.2: 1.5 h
8.1: dmap; 2-azatricyclo[3.3.1.13,7]dec-2-yloxidanyl; [2,2]bipyridinyl; copper(l) chloride / acetonitrile / 0.5 h / 0 °C
9.1: dmap / tetrahydrofuran; toluene / 2 h / 0 °C
10.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 20 °C
11.1: L-Selectride / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere
12.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
12.2: 0.33 h / -20 °C / Inert atmosphere
13.1: dmap; 1,4-diaza-bicyclo[2.2.2]octane / acetonitrile / 76 h / 110 °C
14.1: N-Bromosuccinimide / tetrahydrofuran / 0.83 h / 0 °C
15.1: selenium(IV) oxide / tert-butyl alcohol / 80 °C
15.2: 0.42 h / 150 °C
15.3: 0.5 h / 0 - 20 °C
16.1: caesium carbonate / N,N-dimethyl-formamide / 5.67 h / 20 °C
16.2: 0.58 h / 0 °C
View Scheme
Multi-step reaction with 17 steps
1.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / hexane; dichloromethane / 0.5 h / 0 °C
2.1: diisobutylaluminium hydride / hexane; dichloromethane / 1 h / -93 °C / Inert atmosphere
2.2: (+)-CSA / 0.33 h / 50 °C
3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 20 °C
4.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C / Inert atmosphere
4.2: 0.5 h / 20 °C / Inert atmosphere
5.1: 5,5-dimethyl-1,3-cyclohexadiene / 1.5 h / 110 °C / Inert atmosphere
6.1: tri-n-butyl-tin hydride; 1,1'-azobis(1-cyanocyclohexanenitrile) / 5,5-dimethyl-1,3-cyclohexadiene / 0.17 h / 180 °C / Inert atmosphere; Microwave irradiation
7.1: hydrogenchloride / water; methanol / 3.5 h / 30 °C
7.2: 1.5 h
8.1: hydrogenchloride / methanol; water / 3.5 h / 30 °C
8.2: 1.5 h
9.1: dmap; 2-azatricyclo[3.3.1.13,7]dec-2-yloxidanyl; [2,2]bipyridinyl; copper(l) chloride / acetonitrile / 0.5 h / 0 °C
10.1: dmap / tetrahydrofuran; toluene / 2 h / 0 °C
11.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 20 °C
12.1: L-Selectride / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere
13.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
13.2: 0.33 h / -20 °C / Inert atmosphere
14.1: dmap; 1,4-diaza-bicyclo[2.2.2]octane / acetonitrile / 76 h / 110 °C
15.1: N-Bromosuccinimide / tetrahydrofuran / 0.83 h / 0 °C
16.1: selenium(IV) oxide / tert-butyl alcohol / 80 °C
16.2: 0.42 h / 150 °C
16.3: 0.5 h / 0 - 20 °C
17.1: caesium carbonate / N,N-dimethyl-formamide / 5.67 h / 20 °C
17.2: 0.58 h / 0 °C
View Scheme
C40H54O7Si2

C40H54O7Si2

resiniferatoxin
57444-62-9

resiniferatoxin

Conditions
ConditionsYield
Multi-step reaction with 15 steps
1.1: diisobutylaluminium hydride / hexane; dichloromethane / 1 h / -93 °C / Inert atmosphere
1.2: (+)-CSA / 0.33 h / 50 °C
2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 20 °C
3.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C / Inert atmosphere
3.2: 0.5 h / 20 °C / Inert atmosphere
4.1: 5,5-dimethyl-1,3-cyclohexadiene / 1.5 h / 110 °C / Inert atmosphere
5.1: tri-n-butyl-tin hydride; 1,1'-azobis(1-cyanocyclohexanenitrile) / 5,5-dimethyl-1,3-cyclohexadiene / 0.17 h / 180 °C / Inert atmosphere; Microwave irradiation
6.1: hydrogenchloride / water; methanol / 3.5 h / 30 °C
6.2: 1.5 h
7.1: dmap; 2-azatricyclo[3.3.1.13,7]dec-2-yloxidanyl; [2,2]bipyridinyl; copper(l) chloride / acetonitrile / 0.5 h / 0 °C
8.1: dmap / tetrahydrofuran; toluene / 2 h / 0 °C
9.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 20 °C
10.1: L-Selectride / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere
11.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
11.2: 0.33 h / -20 °C / Inert atmosphere
12.1: dmap; 1,4-diaza-bicyclo[2.2.2]octane / acetonitrile / 76 h / 110 °C
13.1: N-Bromosuccinimide / tetrahydrofuran / 0.83 h / 0 °C
14.1: selenium(IV) oxide / tert-butyl alcohol / 80 °C
14.2: 0.42 h / 150 °C
14.3: 0.5 h / 0 - 20 °C
15.1: caesium carbonate / N,N-dimethyl-formamide / 5.67 h / 20 °C
15.2: 0.58 h / 0 °C
View Scheme
Multi-step reaction with 16 steps
1.1: diisobutylaluminium hydride / hexane; dichloromethane / 1 h / -93 °C / Inert atmosphere
1.2: (+)-CSA / 0.33 h / 50 °C
2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 20 °C
3.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C / Inert atmosphere
3.2: 0.5 h / 20 °C / Inert atmosphere
4.1: 5,5-dimethyl-1,3-cyclohexadiene / 1.5 h / 110 °C / Inert atmosphere
5.1: tri-n-butyl-tin hydride; 1,1'-azobis(1-cyanocyclohexanenitrile) / 5,5-dimethyl-1,3-cyclohexadiene / 0.17 h / 180 °C / Inert atmosphere; Microwave irradiation
6.1: hydrogenchloride / water; methanol / 3.5 h / 30 °C
6.2: 1.5 h
7.1: hydrogenchloride / methanol; water / 3.5 h / 30 °C
7.2: 1.5 h
8.1: dmap; 2-azatricyclo[3.3.1.13,7]dec-2-yloxidanyl; [2,2]bipyridinyl; copper(l) chloride / acetonitrile / 0.5 h / 0 °C
9.1: dmap / tetrahydrofuran; toluene / 2 h / 0 °C
10.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 20 °C
11.1: L-Selectride / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere
12.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
12.2: 0.33 h / -20 °C / Inert atmosphere
13.1: dmap; 1,4-diaza-bicyclo[2.2.2]octane / acetonitrile / 76 h / 110 °C
14.1: N-Bromosuccinimide / tetrahydrofuran / 0.83 h / 0 °C
15.1: selenium(IV) oxide / tert-butyl alcohol / 80 °C
15.2: 0.42 h / 150 °C
15.3: 0.5 h / 0 - 20 °C
16.1: caesium carbonate / N,N-dimethyl-formamide / 5.67 h / 20 °C
16.2: 0.58 h / 0 °C
View Scheme
C44H60O8Si2

C44H60O8Si2

resiniferatoxin
57444-62-9

resiniferatoxin

Conditions
ConditionsYield
Multi-step reaction with 14 steps
1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 20 °C
2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C / Inert atmosphere
2.2: 0.5 h / 20 °C / Inert atmosphere
3.1: 5,5-dimethyl-1,3-cyclohexadiene / 1.5 h / 110 °C / Inert atmosphere
4.1: tri-n-butyl-tin hydride; 1,1'-azobis(1-cyanocyclohexanenitrile) / 5,5-dimethyl-1,3-cyclohexadiene / 0.17 h / 180 °C / Inert atmosphere; Microwave irradiation
5.1: hydrogenchloride / water; methanol / 3.5 h / 30 °C
5.2: 1.5 h
6.1: dmap; 2-azatricyclo[3.3.1.13,7]dec-2-yloxidanyl; [2,2]bipyridinyl; copper(l) chloride / acetonitrile / 0.5 h / 0 °C
7.1: dmap / tetrahydrofuran; toluene / 2 h / 0 °C
8.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 20 °C
9.1: L-Selectride / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere
10.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
10.2: 0.33 h / -20 °C / Inert atmosphere
11.1: dmap; 1,4-diaza-bicyclo[2.2.2]octane / acetonitrile / 76 h / 110 °C
12.1: N-Bromosuccinimide / tetrahydrofuran / 0.83 h / 0 °C
13.1: selenium(IV) oxide / tert-butyl alcohol / 80 °C
13.2: 0.42 h / 150 °C
13.3: 0.5 h / 0 - 20 °C
14.1: caesium carbonate / N,N-dimethyl-formamide / 5.67 h / 20 °C
14.2: 0.58 h / 0 °C
View Scheme
Multi-step reaction with 15 steps
1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 20 °C
2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C / Inert atmosphere
2.2: 0.5 h / 20 °C / Inert atmosphere
3.1: 5,5-dimethyl-1,3-cyclohexadiene / 1.5 h / 110 °C / Inert atmosphere
4.1: tri-n-butyl-tin hydride; 1,1'-azobis(1-cyanocyclohexanenitrile) / 5,5-dimethyl-1,3-cyclohexadiene / 0.17 h / 180 °C / Inert atmosphere; Microwave irradiation
5.1: hydrogenchloride / water; methanol / 3.5 h / 30 °C
5.2: 1.5 h
6.1: hydrogenchloride / methanol; water / 3.5 h / 30 °C
6.2: 1.5 h
7.1: dmap; 2-azatricyclo[3.3.1.13,7]dec-2-yloxidanyl; [2,2]bipyridinyl; copper(l) chloride / acetonitrile / 0.5 h / 0 °C
8.1: dmap / tetrahydrofuran; toluene / 2 h / 0 °C
9.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 20 °C
10.1: L-Selectride / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere
11.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
11.2: 0.33 h / -20 °C / Inert atmosphere
12.1: dmap; 1,4-diaza-bicyclo[2.2.2]octane / acetonitrile / 76 h / 110 °C
13.1: N-Bromosuccinimide / tetrahydrofuran / 0.83 h / 0 °C
14.1: selenium(IV) oxide / tert-butyl alcohol / 80 °C
14.2: 0.42 h / 150 °C
14.3: 0.5 h / 0 - 20 °C
15.1: caesium carbonate / N,N-dimethyl-formamide / 5.67 h / 20 °C
15.2: 0.58 h / 0 °C
View Scheme
C25H34O8

C25H34O8

resiniferatoxin
57444-62-9

resiniferatoxin

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C / Inert atmosphere
1.2: 0.5 h / 20 °C / Inert atmosphere
2.1: 5,5-dimethyl-1,3-cyclohexadiene / 1.5 h / 110 °C / Inert atmosphere
3.1: tri-n-butyl-tin hydride; 1,1'-azobis(1-cyanocyclohexanenitrile) / 5,5-dimethyl-1,3-cyclohexadiene / 0.17 h / 180 °C / Inert atmosphere; Microwave irradiation
4.1: hydrogenchloride / water; methanol / 3.5 h / 30 °C
4.2: 1.5 h
5.1: dmap; 2-azatricyclo[3.3.1.13,7]dec-2-yloxidanyl; [2,2]bipyridinyl; copper(l) chloride / acetonitrile / 0.5 h / 0 °C
6.1: dmap / tetrahydrofuran; toluene / 2 h / 0 °C
7.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 20 °C
8.1: L-Selectride / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere
9.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
9.2: 0.33 h / -20 °C / Inert atmosphere
10.1: dmap; 1,4-diaza-bicyclo[2.2.2]octane / acetonitrile / 76 h / 110 °C
11.1: N-Bromosuccinimide / tetrahydrofuran / 0.83 h / 0 °C
12.1: selenium(IV) oxide / tert-butyl alcohol / 80 °C
12.2: 0.42 h / 150 °C
12.3: 0.5 h / 0 - 20 °C
13.1: caesium carbonate / N,N-dimethyl-formamide / 5.67 h / 20 °C
13.2: 0.58 h / 0 °C
View Scheme
Multi-step reaction with 14 steps
1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C / Inert atmosphere
1.2: 0.5 h / 20 °C / Inert atmosphere
2.1: 5,5-dimethyl-1,3-cyclohexadiene / 1.5 h / 110 °C / Inert atmosphere
3.1: tri-n-butyl-tin hydride; 1,1'-azobis(1-cyanocyclohexanenitrile) / 5,5-dimethyl-1,3-cyclohexadiene / 0.17 h / 180 °C / Inert atmosphere; Microwave irradiation
4.1: hydrogenchloride / water; methanol / 3.5 h / 30 °C
4.2: 1.5 h
5.1: hydrogenchloride / methanol; water / 3.5 h / 30 °C
5.2: 1.5 h
6.1: dmap; 2-azatricyclo[3.3.1.13,7]dec-2-yloxidanyl; [2,2]bipyridinyl; copper(l) chloride / acetonitrile / 0.5 h / 0 °C
7.1: dmap / tetrahydrofuran; toluene / 2 h / 0 °C
8.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 20 °C
9.1: L-Selectride / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere
10.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
10.2: 0.33 h / -20 °C / Inert atmosphere
11.1: dmap; 1,4-diaza-bicyclo[2.2.2]octane / acetonitrile / 76 h / 110 °C
12.1: N-Bromosuccinimide / tetrahydrofuran / 0.83 h / 0 °C
13.1: selenium(IV) oxide / tert-butyl alcohol / 80 °C
13.2: 0.42 h / 150 °C
13.3: 0.5 h / 0 - 20 °C
14.1: caesium carbonate / N,N-dimethyl-formamide / 5.67 h / 20 °C
14.2: 0.58 h / 0 °C
View Scheme
C29H38O8S4

C29H38O8S4

resiniferatoxin
57444-62-9

resiniferatoxin

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1.1: 5,5-dimethyl-1,3-cyclohexadiene / 1.5 h / 110 °C / Inert atmosphere
2.1: tri-n-butyl-tin hydride; 1,1'-azobis(1-cyanocyclohexanenitrile) / 5,5-dimethyl-1,3-cyclohexadiene / 0.17 h / 180 °C / Inert atmosphere; Microwave irradiation
3.1: hydrogenchloride / water; methanol / 3.5 h / 30 °C
3.2: 1.5 h
4.1: dmap; 2-azatricyclo[3.3.1.13,7]dec-2-yloxidanyl; [2,2]bipyridinyl; copper(l) chloride / acetonitrile / 0.5 h / 0 °C
5.1: dmap / tetrahydrofuran; toluene / 2 h / 0 °C
6.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 20 °C
7.1: L-Selectride / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere
8.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
8.2: 0.33 h / -20 °C / Inert atmosphere
9.1: dmap; 1,4-diaza-bicyclo[2.2.2]octane / acetonitrile / 76 h / 110 °C
10.1: N-Bromosuccinimide / tetrahydrofuran / 0.83 h / 0 °C
11.1: selenium(IV) oxide / tert-butyl alcohol / 80 °C
11.2: 0.42 h / 150 °C
11.3: 0.5 h / 0 - 20 °C
12.1: caesium carbonate / N,N-dimethyl-formamide / 5.67 h / 20 °C
12.2: 0.58 h / 0 °C
View Scheme
Multi-step reaction with 13 steps
1.1: 5,5-dimethyl-1,3-cyclohexadiene / 1.5 h / 110 °C / Inert atmosphere
2.1: tri-n-butyl-tin hydride; 1,1'-azobis(1-cyanocyclohexanenitrile) / 5,5-dimethyl-1,3-cyclohexadiene / 0.17 h / 180 °C / Inert atmosphere; Microwave irradiation
3.1: hydrogenchloride / water; methanol / 3.5 h / 30 °C
3.2: 1.5 h
4.1: hydrogenchloride / methanol; water / 3.5 h / 30 °C
4.2: 1.5 h
5.1: dmap; 2-azatricyclo[3.3.1.13,7]dec-2-yloxidanyl; [2,2]bipyridinyl; copper(l) chloride / acetonitrile / 0.5 h / 0 °C
6.1: dmap / tetrahydrofuran; toluene / 2 h / 0 °C
7.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 20 °C
8.1: L-Selectride / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere
9.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
9.2: 0.33 h / -20 °C / Inert atmosphere
10.1: dmap; 1,4-diaza-bicyclo[2.2.2]octane / acetonitrile / 76 h / 110 °C
11.1: N-Bromosuccinimide / tetrahydrofuran / 0.83 h / 0 °C
12.1: selenium(IV) oxide / tert-butyl alcohol / 80 °C
12.2: 0.42 h / 150 °C
12.3: 0.5 h / 0 - 20 °C
13.1: caesium carbonate / N,N-dimethyl-formamide / 5.67 h / 20 °C
13.2: 0.58 h / 0 °C
View Scheme
C25H32O6

C25H32O6

resiniferatoxin
57444-62-9

resiniferatoxin

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: hydrogenchloride / water; methanol / 3.5 h / 30 °C
1.2: 1.5 h
2.1: dmap; 2-azatricyclo[3.3.1.13,7]dec-2-yloxidanyl; [2,2]bipyridinyl; copper(l) chloride / acetonitrile / 0.5 h / 0 °C
3.1: dmap / tetrahydrofuran; toluene / 2 h / 0 °C
4.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 20 °C
5.1: L-Selectride / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere
6.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
6.2: 0.33 h / -20 °C / Inert atmosphere
7.1: dmap; 1,4-diaza-bicyclo[2.2.2]octane / acetonitrile / 76 h / 110 °C
8.1: N-Bromosuccinimide / tetrahydrofuran / 0.83 h / 0 °C
9.1: selenium(IV) oxide / tert-butyl alcohol / 80 °C
9.2: 0.42 h / 150 °C
9.3: 0.5 h / 0 - 20 °C
10.1: caesium carbonate / N,N-dimethyl-formamide / 5.67 h / 20 °C
10.2: 0.58 h / 0 °C
View Scheme
Multi-step reaction with 11 steps
1.1: hydrogenchloride / water; methanol / 3.5 h / 30 °C
1.2: 1.5 h
2.1: hydrogenchloride / methanol; water / 3.5 h / 30 °C
2.2: 1.5 h
3.1: dmap; 2-azatricyclo[3.3.1.13,7]dec-2-yloxidanyl; [2,2]bipyridinyl; copper(l) chloride / acetonitrile / 0.5 h / 0 °C
4.1: dmap / tetrahydrofuran; toluene / 2 h / 0 °C
5.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 20 °C
6.1: L-Selectride / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere
7.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
7.2: 0.33 h / -20 °C / Inert atmosphere
8.1: dmap; 1,4-diaza-bicyclo[2.2.2]octane / acetonitrile / 76 h / 110 °C
9.1: N-Bromosuccinimide / tetrahydrofuran / 0.83 h / 0 °C
10.1: selenium(IV) oxide / tert-butyl alcohol / 80 °C
10.2: 0.42 h / 150 °C
10.3: 0.5 h / 0 - 20 °C
11.1: caesium carbonate / N,N-dimethyl-formamide / 5.67 h / 20 °C
11.2: 0.58 h / 0 °C
View Scheme
C12H20O4

C12H20O4

resiniferatoxin
57444-62-9

resiniferatoxin

Conditions
ConditionsYield
Multi-step reaction with 37 steps
1.1: p-benzoquinone; Hoveyda-Grubbs catalyst second generation / 1,2-dichloro-ethane / 9 h / 80 °C / Inert atmosphere
2.1: hydrogen; palladium 10% on activated carbon / hexane; ethyl acetate / 0.5 h / 0 °C / 760.05 Torr
3.1: tert.-butyl lithium / tetrahydrofuran; pentane / 0.17 h / -78 - 0 °C / Inert atmosphere
3.2: 0.17 h / -78 - 0 °C / Inert atmosphere
4.1: 4-methylmorpholine N-oxide; tetra-n-propylammonium perruthenate. / dichloromethane / 0.75 h / 20 °C / Molecular sieve; Inert atmosphere
5.1: tert.-butyl lithium / tetrahydrofuran; pentane / 15 h / -78 °C / Inert atmosphere
5.2: 0.17 h / -78 °C / Inert atmosphere
5.3: 2 h / -78 - -45 °C / Inert atmosphere
6.1: Dowex 50W / tetrahydrofuran; water / 12 h / 90 °C
7.1: pyridine / dichloromethane / 1 h / 0 - 20 °C
8.1: (+)-CSA / benzene / 2 h / 20 °C / Inert atmosphere
9.1: triethylamine / dichloromethane / 0.75 h / 20 °C / Inert atmosphere
10.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 °C
10.2: 0.42 h
11.1: lead(IV) tetraacetate; potassium carbonate / toluene / 1.17 h / 0 - 20 °C
12.1: triethylamine / dichloromethane / 1.25 h / 0 °C
13.1: dmap / toluene / 1.5 h / 20 °C / Darkness
14.1: sodium hydrogencarbonate / toluene / 0.5 h / 20 °C / Irradiation
15.1: potassium carbonate / methanol / 7.5 h / 0 °C
16.1: acetic anhydride; dimethyl sulfoxide / 2 h / 35 °C
17.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol / 0.17 h / -78 °C
18.1: 2,6-dimethylpyridine / water; dichloromethane / 0.5 h / 0 °C
19.1: 1,1'-azobis(1-cyanocyclohexanenitrile) / chlorobenzene / 0.5 h / Reflux; Inert atmosphere
20.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
21.1: triethylamine / dichloromethane / 1.5 h / 0 °C
22.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / hexane; dichloromethane / 0.5 h / 0 °C
23.1: diisobutylaluminium hydride / hexane; dichloromethane / 1 h / -93 °C / Inert atmosphere
23.2: (+)-CSA / 0.33 h / 50 °C
24.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 20 °C
25.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C / Inert atmosphere
25.2: 0.5 h / 20 °C / Inert atmosphere
26.1: 5,5-dimethyl-1,3-cyclohexadiene / 1.5 h / 110 °C / Inert atmosphere
27.1: tri-n-butyl-tin hydride; 1,1'-azobis(1-cyanocyclohexanenitrile) / 5,5-dimethyl-1,3-cyclohexadiene / 0.17 h / 180 °C / Inert atmosphere; Microwave irradiation
28.1: hydrogenchloride / water; methanol / 3.5 h / 30 °C
28.2: 1.5 h
29.1: dmap; 2-azatricyclo[3.3.1.13,7]dec-2-yloxidanyl; [2,2]bipyridinyl; copper(l) chloride / acetonitrile / 0.5 h / 0 °C
30.1: dmap / tetrahydrofuran; toluene / 2 h / 0 °C
31.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 20 °C
32.1: L-Selectride / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere
33.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
33.2: 0.33 h / -20 °C / Inert atmosphere
34.1: dmap; 1,4-diaza-bicyclo[2.2.2]octane / acetonitrile / 76 h / 110 °C
35.1: N-Bromosuccinimide / tetrahydrofuran / 0.83 h / 0 °C
36.1: selenium(IV) oxide / tert-butyl alcohol / 80 °C
36.2: 0.42 h / 150 °C
36.3: 0.5 h / 0 - 20 °C
37.1: caesium carbonate / N,N-dimethyl-formamide / 5.67 h / 20 °C
37.2: 0.58 h / 0 °C
View Scheme
Multi-step reaction with 38 steps
1.1: p-benzoquinone; Hoveyda-Grubbs catalyst second generation / 1,2-dichloro-ethane / 9 h / 80 °C / Inert atmosphere
2.1: hydrogen; palladium 10% on activated carbon / hexane; ethyl acetate / 0.5 h / 0 °C / 760.05 Torr
3.1: tert.-butyl lithium / tetrahydrofuran; pentane / 0.17 h / -78 - 0 °C / Inert atmosphere
3.2: 0.17 h / -78 - 0 °C / Inert atmosphere
4.1: 4-methylmorpholine N-oxide; tetra-n-propylammonium perruthenate. / dichloromethane / 0.75 h / 20 °C / Molecular sieve; Inert atmosphere
5.1: tert.-butyl lithium / tetrahydrofuran; pentane / 15 h / -78 °C / Inert atmosphere
5.2: 0.17 h / -78 °C / Inert atmosphere
5.3: 2 h / -78 - -45 °C / Inert atmosphere
6.1: Dowex 50W / tetrahydrofuran; water / 12 h / 90 °C
7.1: pyridine / dichloromethane / 1 h / 0 - 20 °C
8.1: (+)-CSA / benzene / 2 h / 20 °C / Inert atmosphere
9.1: triethylamine / dichloromethane / 0.75 h / 20 °C / Inert atmosphere
10.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 °C
10.2: 0.42 h
11.1: lead(IV) tetraacetate; potassium carbonate / toluene / 1.17 h / 0 - 20 °C
12.1: triethylamine / dichloromethane / 1.25 h / 0 °C
13.1: dmap / toluene / 1.5 h / 20 °C / Darkness
14.1: sodium hydrogencarbonate / toluene / 0.5 h / 20 °C / Irradiation
15.1: potassium carbonate / methanol / 7.5 h / 0 °C
16.1: acetic anhydride; dimethyl sulfoxide / 2 h / 35 °C
17.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol / 0.17 h / -78 °C
18.1: 2,6-dimethylpyridine / water; dichloromethane / 0.5 h / 0 °C
19.1: 1,1'-azobis(1-cyanocyclohexanenitrile) / chlorobenzene / 0.5 h / Reflux; Inert atmosphere
20.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
21.1: triethylamine / dichloromethane / 1.5 h / 0 °C
22.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / hexane; dichloromethane / 0.5 h / 0 °C
23.1: diisobutylaluminium hydride / hexane; dichloromethane / 1 h / -93 °C / Inert atmosphere
23.2: (+)-CSA / 0.33 h / 50 °C
24.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 20 °C
25.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C / Inert atmosphere
25.2: 0.5 h / 20 °C / Inert atmosphere
26.1: 5,5-dimethyl-1,3-cyclohexadiene / 1.5 h / 110 °C / Inert atmosphere
27.1: tri-n-butyl-tin hydride; 1,1'-azobis(1-cyanocyclohexanenitrile) / 5,5-dimethyl-1,3-cyclohexadiene / 0.17 h / 180 °C / Inert atmosphere; Microwave irradiation
28.1: hydrogenchloride / water; methanol / 3.5 h / 30 °C
28.2: 1.5 h
29.1: hydrogenchloride / methanol; water / 3.5 h / 30 °C
29.2: 1.5 h
30.1: dmap; 2-azatricyclo[3.3.1.13,7]dec-2-yloxidanyl; [2,2]bipyridinyl; copper(l) chloride / acetonitrile / 0.5 h / 0 °C
31.1: dmap / tetrahydrofuran; toluene / 2 h / 0 °C
32.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 20 °C
33.1: L-Selectride / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere
34.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
34.2: 0.33 h / -20 °C / Inert atmosphere
35.1: dmap; 1,4-diaza-bicyclo[2.2.2]octane / acetonitrile / 76 h / 110 °C
36.1: N-Bromosuccinimide / tetrahydrofuran / 0.83 h / 0 °C
37.1: selenium(IV) oxide / tert-butyl alcohol / 80 °C
37.2: 0.42 h / 150 °C
37.3: 0.5 h / 0 - 20 °C
38.1: caesium carbonate / N,N-dimethyl-formamide / 5.67 h / 20 °C
38.2: 0.58 h / 0 °C
View Scheme
C19H28O5

C19H28O5

resiniferatoxin
57444-62-9

resiniferatoxin

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: dmap; 2-azatricyclo[3.3.1.13,7]dec-2-yloxidanyl; [2,2]bipyridinyl; copper(l) chloride / acetonitrile / 0.5 h / 0 °C
2.1: dmap / tetrahydrofuran; toluene / 2 h / 0 °C
3.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 20 °C
4.1: L-Selectride / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere
5.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
5.2: 0.33 h / -20 °C / Inert atmosphere
6.1: dmap; 1,4-diaza-bicyclo[2.2.2]octane / acetonitrile / 76 h / 110 °C
7.1: N-Bromosuccinimide / tetrahydrofuran / 0.83 h / 0 °C
8.1: selenium(IV) oxide / tert-butyl alcohol / 80 °C
8.2: 0.42 h / 150 °C
8.3: 0.5 h / 0 - 20 °C
9.1: caesium carbonate / N,N-dimethyl-formamide / 5.67 h / 20 °C
9.2: 0.58 h / 0 °C
View Scheme
C21H28O5

C21H28O5

resiniferatoxin
57444-62-9

resiniferatoxin

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: hydrogenchloride / methanol; water / 3.5 h / 30 °C
1.2: 1.5 h
2.1: dmap; 2-azatricyclo[3.3.1.13,7]dec-2-yloxidanyl; [2,2]bipyridinyl; copper(l) chloride / acetonitrile / 0.5 h / 0 °C
3.1: dmap / tetrahydrofuran; toluene / 2 h / 0 °C
4.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 20 °C
5.1: L-Selectride / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere
6.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
6.2: 0.33 h / -20 °C / Inert atmosphere
7.1: dmap; 1,4-diaza-bicyclo[2.2.2]octane / acetonitrile / 76 h / 110 °C
8.1: N-Bromosuccinimide / tetrahydrofuran / 0.83 h / 0 °C
9.1: selenium(IV) oxide / tert-butyl alcohol / 80 °C
9.2: 0.42 h / 150 °C
9.3: 0.5 h / 0 - 20 °C
10.1: caesium carbonate / N,N-dimethyl-formamide / 5.67 h / 20 °C
10.2: 0.58 h / 0 °C
View Scheme
resiniferatoxin
57444-62-9

resiniferatoxin

9,13,14-orthophenylacetyl-3β-hydroxyresiniferonyl 20-(4-hydroxy-3-methoxyphenylacetate)

9,13,14-orthophenylacetyl-3β-hydroxyresiniferonyl 20-(4-hydroxy-3-methoxyphenylacetate)

Conditions
ConditionsYield
With sodium tetrahydroborate In ethanol for 2h;60%
resiniferatoxin
57444-62-9

resiniferatoxin

Resininiferonol-9-13-14-ortho-phenyl acetate

Resininiferonol-9-13-14-ortho-phenyl acetate

Conditions
ConditionsYield
With sodium methylate In methanol

Resiniferatoxin Chemical Properties

Molecule structure of Resiniferatoxin (CAS NO.57444-62-9) :

Molecular Weight: 628.7081 g/mol
Molecular Formula: C37H40O9 
Density: 1.35 g/cm3 
Boiling Point: 768.7 °C at 760 mmHg 
Flash Point: 240.3 °C
Index of Refraction: 1.643
Molar Refractivity: 167.86 cm3
Molar Volume: 463.9 cm3
Polarizability: 66.54×10-24 cm3
Surface Tension: 62.4 dyne/cm 
Enthalpy of Vaporization: 117.42 kJ/mol
Vapour Pressure: 7.41E-25 mmHg at 25 °C 
Storage Temp.: −20 °C
XLogP3-AA: 4.5
H-Bond Donor: 2
H-Bond Acceptor: 9
Rotatable Bond Count: 9
Tautomer Count: 9
Exact Mass: 628.267233
MonoIsotopic Mass: 628.267233
Topological Polar Surface Area: 121
Heavy Atom Count: 46
Complexity: 1330
Defined Atom StereoCenter Count: 7
Undefined Atom StereoCenter Count: 1 
Canonical SMILES: CC1CC2(C3C4C1(C5C=C(C(=O)C5(CC(=C4)COC(=O)CC6=C(C=C(C=C6)O)OC)O)C)OC(O3)(O2)CC7=CC=CC=C7)C(=C)C
Isomeric SMILES: C[C@@H]1C[C@]2([C@H]3[C@H]4[C@]1([C@@H]5C=C(C(=O)[C@]5(CC(=C4)COC(=O)
CC6=C(C=C(C=C6)O)OC)O)C)OC(O3)(O2)CC7=CC=CC=C7)C(=C)C
InChI: InChI=1S/C37H40O9/c1-21(2)35-17-23(4)37-28(33(35)44-36(45-35,46-37)19-24-9-7-6-8-10-24)14-25(18-34(41)30(37)13-22(3)32(34)40)20-43-31(39)15-26-11-12-27(38)16-29(26)42-5/h6-14,16,23,28,30,33,38,41H,1,15,
17-20H2,2-5H3/t23-,28+,30-,33-,34-,35-,36?,37-/m1/s1
InChIKey: OYWHJFQVSOUQSF-PKRQWDGKSA-N
Product Categories of Resiniferatoxin (CAS NO.57444-62-9) : Vanilloids; Neurobiology; Pharmacologicals; Vanilloid/TRPV channel

Resiniferatoxin Toxicity Data With Reference

1.    

ice-unr TDLo: 50 ng/kg

     EJPHAZ    European Journal of Pharmacology. 422 (2001),185.

Resiniferatoxin Safety Profile

A poison by intracerebral route. When heated to decomposition it emits acrid smoke and irritating vapors.
Hazard Codes: ToxicT
Risk Statements: 25-35 
R25 :Toxic if swallowed. 
R35:Causes severe burns.
Safety Statements: 26-36/37/39-45
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
RIDADR: UN 2928 6.1/PG 2
WGK Germany: 3
RTECS: CY1633700
F: 10-23
HazardClass: 6.1(a)
PackingGroup: II 

Resiniferatoxin Specification

 Resiniferatoxin (CAS NO.57444-62-9) is also called RTX ; 6,7-Deepoxy-6,7-didehydro-5-deoxy-21-dephenyl-21-
(phenylmethyl)daphnetoxin 20-(3-hydroxy-5-methoxybenzeneacetate) ; Benzeneacetic acid, 4-hydroxy-3-methoxy-, ((2S,3aR,3bS,6aR,9aR,9bR,10R,11aR)-3a,3b,6,6a,9a,10,11,11a-octahydro-6a-hydroxy-8,10-dimethyl-11a-(1-methylethenyl)-7-oxo-2-(phenylmethyl)-7H-2,9b-epoxyazuleno(5,4-e)-1,3-benzodioxol-5-yl)methyl ester . Resiniferatoxin (CAS NO.57444-62-9) is white to off-white solid.

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