Ingenol supplier | CasNO.30220-46-3

Name
INGENOL
EINECS
CAS No. 30220-46-3
Article Data14
CAS DataBase
Density 1.33 g/cm³
Solubility
Melting Point 153 °C
Formula C₂₀H₂₈O₅
Boiling Point 523.785 °C at 760 mmHg
Molecular Weight 348.439
Flash Point 284.654 °C
Transport Information
Appearance
Safety 26-36
Risk Codes 38-41
Molecular Structure
Hazard Symbols Xi
Synonyms 1H-2,8a-Methanocyclopenta[a]cyclopropa[e]cyclodecen-11-one,1a,2,5,5a,6,9,10,10a-octahydro-5,5a,6-trihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-,[1aR-(1aa,2b,5b,5ab,6b,8aa,9a,10aa)]-;Ingenol;
PSA 97.99000
LogP 0.81520

Synthetic route

: 54706-99-9
(1aR,2S,5R,5aS,6S,8aS,9R,10aR)-5,5a,6-trihydroxy-1,1,4,7,9-pentamethyl-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-11-one

: 30220-46-3
ingenol

Conditions

Conditions	Yield
With selenium(IV) oxide; formic acid In 1,4-dioxane at 80℃; for 1.25h;	76%
Stage #1: (1aR,2S,5R,5aS,6S,8aS,9R,10aR)-5,5a,6-trihydroxy-1,1,4,7,9-pentamethyl-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-11-one With selenium(IV) oxide; formic acid In 1,4-dioxane at 80℃; for 2h; Inert atmosphere; Stage #2: With sodium hydroxide In 1,4-dioxane; water for 0.5h; Inert atmosphere;	76%
With selenium(IV) oxide In 1,4-dioxane; formic acid at 80℃; for 2h;	70%
With selenium(IV) oxide; silica gel In tetrahydrofuran at 80℃; for 2h;	40%

: 64280-37-1
ingenol monoacetate

: 30220-46-3
ingenol

Conditions

Conditions	Yield
With potassium hydroxide In methanol; water at 0 - 20℃; Temperature; Solvent; Inert atmosphere;	74%

: 30220-45-2
ingenol 3,5,20-triacetate

: 30220-46-3
ingenol

Conditions

Conditions	Yield
With sodium methylate In methanol	71%

: 77573-43-4
(6S,6aR,7aR,9R,9aS,12S,12aR,12bR)-12,12a-dihydroxy-2,2,7,7,9,11-hexamethyl-4,6,6a,7,7a,8,9,12,12a,12b-decahydro-6,9a-methanocyclopenta[9,10]cyclopropa[5,6]cyclodeca[1,2-d][1,3]dioxin-13-one

A: 30220-46-3
ingenol

B: Ingenol-3,4-acetonid

Conditions

Conditions	Yield
With perchloric acid In methanol for 1h;	A 66% B n/a

: 77573-44-5
ingenol-3,4:5,20-diacetonide

A: 30220-46-3
ingenol

B: 77573-43-4
(6S,6aR,7aR,9R,9aS,12S,12aR,12bR)-12,12a-dihydroxy-2,2,7,7,9,11-hexamethyl-4,6,6a,7,7a,8,9,12,12a,12b-decahydro-6,9a-methanocyclopenta[9,10]cyclopropa[5,6]cyclodeca[1,2-d][1,3]dioxin-13-one

C: Ingenol-3,4-acetonid

Conditions

Conditions	Yield
With perchloric acid In methanol for 0.75h; Further byproducts given;	A 31% B 3% C 18%

...Expand

: 49620-09-9
C43H47N3O9

: 30220-46-3
ingenol

Conditions

Conditions	Yield
With sodium methylate In methanol

: 42483-56-7
ingenol 3-(2,4,6,8,10)-tetradecapentaenoate

: 30220-46-3
ingenol

Conditions

Conditions	Yield
With sodium methylate In methanol

: ingenol-3-(t-butyldimethyl)silyl ether

: 30220-46-3
ingenol

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran for 0.5h;

: 20-O-Isobutyryl-ingenol

: 30220-46-3
ingenol

Conditions

Conditions	Yield
With potassium hydroxide In methanol for 0.5h; Yield given;

: 3-O-Propionyl-20-O-(S)-(2'-methyl)butyryl-ingenol

A: 30220-46-3
ingenol

B: 20-O-(S)-(2'-Methyl)butyryl-ingenol

Conditions

Conditions	Yield
With sodium methylate In methanol for 0.666667h; Ambient temperature; Yield given. Yields of byproduct given;

: 91413-76-2
3,4-O-isopropylidene-20-deoxyingenol

: 30220-46-3
ingenol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C 2: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C View Scheme

: C20H30O3

: 30220-46-3
ingenol

Conditions

Conditions	Yield
Multi-step reaction with 21 steps 1.1: 98 percent / KH / tetrahydrofuran / Heating 2.1: 76 percent / Hoveyda-Grubbs catalyst / toluene / 30 h / Heating 3.1: aq. HCl / tetrahydrofuran / 3 h / Heating 4.1: 1.9 g / NaBH4 / ethanol; tetrahydrofuran / 0.25 h / 0 °C 5.1: PPh3; imidazole; I2 / tetrahydrofuran / 3 h / 0 °C 5.2: 94 percent / t-BuOK / tetrahydrofuran; dimethylsulfoxide / 20 °C 6.1: 49 percent / SeO2; aq. AcOH; t-BuOOH / CH2Cl2; decane / 2 h / 20 °C 7.1: 74 percent / Dess-Martin periodinane / CH2Cl2 / 1.5 h / -40 - 10 °C 8.1: 74 percent / aq. RhCl3 / aq. ethanol / 0.58 h / 115 °C 9.1: 94 percent / P(OMe)3; O2; t-BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / 0.75 h / -40 °C 10.1: 73 percent / VO(acac)2; t-BuOOH / benzene; decane / 10 h / 20 °C 11.1: 72 percent / Et3N / CH2Cl2 / 1 h / -10 - -5 °C 12.1: NaBH4 / methanol / 5 h / 20 °C 13.1: 39 mg / PPTS / CH2Cl2 / 0.5 h / Heating 14.1: 90 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 18 h / 20 °C 15.1: 96 percent / Et3N / CH2Cl2 / 0.75 h / -78 °C 16.1: 76 percent / Li2CO3 / dimethylformamide / 5 h / 55 °C 17.1: 97 percent / (NH4)6Mo7O24; aq. H2O2 / aq. ethanol / 6 h / 20 °C 18.1: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating 19.1: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C 20.1: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C 21.1: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C View Scheme

Yield

Multi-step reaction with 21 steps
1.1: 98 percent / KH / tetrahydrofuran / Heating
2.1: 76 percent / Hoveyda-Grubbs catalyst / toluene / 30 h / Heating
3.1: aq. HCl / tetrahydrofuran / 3 h / Heating
4.1: 1.9 g / NaBH4 / ethanol; tetrahydrofuran / 0.25 h / 0 °C
5.1: PPh3; imidazole; I2 / tetrahydrofuran / 3 h / 0 °C
5.2: 94 percent / t-BuOK / tetrahydrofuran; dimethylsulfoxide / 20 °C
6.1: 49 percent / SeO2; aq. AcOH; t-BuOOH / CH2Cl2; decane / 2 h / 20 °C
7.1: 74 percent / Dess-Martin periodinane / CH2Cl2 / 1.5 h / -40 - 10 °C
8.1: 74 percent / aq. RhCl3 / aq. ethanol / 0.58 h / 115 °C
9.1: 94 percent / P(OMe)3; O2; t-BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / 0.75 h / -40 °C
10.1: 73 percent / VO(acac)2; t-BuOOH / benzene; decane / 10 h / 20 °C
11.1: 72 percent / Et3N / CH2Cl2 / 1 h / -10 - -5 °C
12.1: NaBH4 / methanol / 5 h / 20 °C
13.1: 39 mg / PPTS / CH2Cl2 / 0.5 h / Heating
14.1: 90 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 18 h / 20 °C
15.1: 96 percent / Et3N / CH2Cl2 / 0.75 h / -78 °C
16.1: 76 percent / Li2CO3 / dimethylformamide / 5 h / 55 °C
17.1: 97 percent / (NH4)6Mo7O24; aq. H2O2 / aq. ethanol / 6 h / 20 °C
18.1: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating
19.1: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C
20.1: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C
21.1: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C
View Scheme

: 827325-49-5
C23H32O5

: 30220-46-3
ingenol

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 96 percent / Et3N / CH2Cl2 / 0.75 h / -78 °C 2: 76 percent / Li2CO3 / dimethylformamide / 5 h / 55 °C 3: 97 percent / (NH4)6Mo7O24; aq. H2O2 / aq. ethanol / 6 h / 20 °C 4: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating 5: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C 6: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C 7: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C View Scheme

Yield

Multi-step reaction with 7 steps
1: 96 percent / Et3N / CH2Cl2 / 0.75 h / -78 °C
2: 76 percent / Li2CO3 / dimethylformamide / 5 h / 55 °C
3: 97 percent / (NH4)6Mo7O24; aq. H2O2 / aq. ethanol / 6 h / 20 °C
4: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating
5: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C
6: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C
7: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C
View Scheme

: 827325-41-7
C28H34O4

: 30220-46-3
ingenol

Conditions

Conditions	Yield
Multi-step reaction with 13 steps 1: 94 percent / P(OMe)3; O2; t-BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / 0.75 h / -40 °C 2: 73 percent / VO(acac)2; t-BuOOH / benzene; decane / 10 h / 20 °C 3: 72 percent / Et3N / CH2Cl2 / 1 h / -10 - -5 °C 4: NaBH4 / methanol / 5 h / 20 °C 5: 39 mg / PPTS / CH2Cl2 / 0.5 h / Heating 6: 90 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 18 h / 20 °C 7: 96 percent / Et3N / CH2Cl2 / 0.75 h / -78 °C 8: 76 percent / Li2CO3 / dimethylformamide / 5 h / 55 °C 9: 97 percent / (NH4)6Mo7O24; aq. H2O2 / aq. ethanol / 6 h / 20 °C 10: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating 11: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C 12: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C 13: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C View Scheme

Yield

Multi-step reaction with 13 steps
1: 94 percent / P(OMe)3; O2; t-BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / 0.75 h / -40 °C
2: 73 percent / VO(acac)2; t-BuOOH / benzene; decane / 10 h / 20 °C
3: 72 percent / Et3N / CH2Cl2 / 1 h / -10 - -5 °C
4: NaBH4 / methanol / 5 h / 20 °C
5: 39 mg / PPTS / CH2Cl2 / 0.5 h / Heating
6: 90 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 18 h / 20 °C
7: 96 percent / Et3N / CH2Cl2 / 0.75 h / -78 °C
8: 76 percent / Li2CO3 / dimethylformamide / 5 h / 55 °C
9: 97 percent / (NH4)6Mo7O24; aq. H2O2 / aq. ethanol / 6 h / 20 °C
10: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating
11: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C
12: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C
13: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C
View Scheme

: C28H36O4

: 30220-46-3
ingenol

Conditions

Conditions	Yield
Multi-step reaction with 18 steps 1.1: 1.9 g / NaBH4 / ethanol; tetrahydrofuran / 0.25 h / 0 °C 2.1: PPh3; imidazole; I2 / tetrahydrofuran / 3 h / 0 °C 2.2: 94 percent / t-BuOK / tetrahydrofuran; dimethylsulfoxide / 20 °C 3.1: 49 percent / SeO2; aq. AcOH; t-BuOOH / CH2Cl2; decane / 2 h / 20 °C 4.1: 74 percent / Dess-Martin periodinane / CH2Cl2 / 1.5 h / -40 - 10 °C 5.1: 74 percent / aq. RhCl3 / aq. ethanol / 0.58 h / 115 °C 6.1: 94 percent / P(OMe)3; O2; t-BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / 0.75 h / -40 °C 7.1: 73 percent / VO(acac)2; t-BuOOH / benzene; decane / 10 h / 20 °C 8.1: 72 percent / Et3N / CH2Cl2 / 1 h / -10 - -5 °C 9.1: NaBH4 / methanol / 5 h / 20 °C 10.1: 39 mg / PPTS / CH2Cl2 / 0.5 h / Heating 11.1: 90 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 18 h / 20 °C 12.1: 96 percent / Et3N / CH2Cl2 / 0.75 h / -78 °C 13.1: 76 percent / Li2CO3 / dimethylformamide / 5 h / 55 °C 14.1: 97 percent / (NH4)6Mo7O24; aq. H2O2 / aq. ethanol / 6 h / 20 °C 15.1: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating 16.1: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C 17.1: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C 18.1: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C View Scheme

Yield

Multi-step reaction with 18 steps
1.1: 1.9 g / NaBH4 / ethanol; tetrahydrofuran / 0.25 h / 0 °C
2.1: PPh3; imidazole; I2 / tetrahydrofuran / 3 h / 0 °C
2.2: 94 percent / t-BuOK / tetrahydrofuran; dimethylsulfoxide / 20 °C
3.1: 49 percent / SeO2; aq. AcOH; t-BuOOH / CH2Cl2; decane / 2 h / 20 °C
4.1: 74 percent / Dess-Martin periodinane / CH2Cl2 / 1.5 h / -40 - 10 °C
5.1: 74 percent / aq. RhCl3 / aq. ethanol / 0.58 h / 115 °C
6.1: 94 percent / P(OMe)3; O2; t-BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / 0.75 h / -40 °C
7.1: 73 percent / VO(acac)2; t-BuOOH / benzene; decane / 10 h / 20 °C
8.1: 72 percent / Et3N / CH2Cl2 / 1 h / -10 - -5 °C
9.1: NaBH4 / methanol / 5 h / 20 °C
10.1: 39 mg / PPTS / CH2Cl2 / 0.5 h / Heating
11.1: 90 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 18 h / 20 °C
12.1: 96 percent / Et3N / CH2Cl2 / 0.75 h / -78 °C
13.1: 76 percent / Li2CO3 / dimethylformamide / 5 h / 55 °C
14.1: 97 percent / (NH4)6Mo7O24; aq. H2O2 / aq. ethanol / 6 h / 20 °C
15.1: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating
16.1: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C
17.1: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C
18.1: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C
View Scheme

: 827325-50-8
C24H34O7S

: 30220-46-3
ingenol

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 76 percent / Li2CO3 / dimethylformamide / 5 h / 55 °C 2: 97 percent / (NH4)6Mo7O24; aq. H2O2 / aq. ethanol / 6 h / 20 °C 3: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating 4: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C 5: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C 6: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C View Scheme

Yield

Multi-step reaction with 6 steps
1: 76 percent / Li2CO3 / dimethylformamide / 5 h / 55 °C
2: 97 percent / (NH4)6Mo7O24; aq. H2O2 / aq. ethanol / 6 h / 20 °C
3: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating
4: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C
5: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C
6: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C
View Scheme

: 827325-39-3
C28H36O3

: 30220-46-3
ingenol

Conditions

Conditions	Yield
Multi-step reaction with 16 steps 1: 49 percent / SeO2; aq. AcOH; t-BuOOH / CH2Cl2; decane / 2 h / 20 °C 2: 74 percent / Dess-Martin periodinane / CH2Cl2 / 1.5 h / -40 - 10 °C 3: 74 percent / aq. RhCl3 / aq. ethanol / 0.58 h / 115 °C 4: 94 percent / P(OMe)3; O2; t-BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / 0.75 h / -40 °C 5: 73 percent / VO(acac)2; t-BuOOH / benzene; decane / 10 h / 20 °C 6: 72 percent / Et3N / CH2Cl2 / 1 h / -10 - -5 °C 7: NaBH4 / methanol / 5 h / 20 °C 8: 39 mg / PPTS / CH2Cl2 / 0.5 h / Heating 9: 90 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 18 h / 20 °C 10: 96 percent / Et3N / CH2Cl2 / 0.75 h / -78 °C 11: 76 percent / Li2CO3 / dimethylformamide / 5 h / 55 °C 12: 97 percent / (NH4)6Mo7O24; aq. H2O2 / aq. ethanol / 6 h / 20 °C 13: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating 14: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C 15: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C 16: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C View Scheme

Yield

Multi-step reaction with 16 steps
1: 49 percent / SeO2; aq. AcOH; t-BuOOH / CH2Cl2; decane / 2 h / 20 °C
2: 74 percent / Dess-Martin periodinane / CH2Cl2 / 1.5 h / -40 - 10 °C
3: 74 percent / aq. RhCl3 / aq. ethanol / 0.58 h / 115 °C
4: 94 percent / P(OMe)3; O2; t-BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / 0.75 h / -40 °C
5: 73 percent / VO(acac)2; t-BuOOH / benzene; decane / 10 h / 20 °C
6: 72 percent / Et3N / CH2Cl2 / 1 h / -10 - -5 °C
7: NaBH4 / methanol / 5 h / 20 °C
8: 39 mg / PPTS / CH2Cl2 / 0.5 h / Heating
9: 90 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 18 h / 20 °C
10: 96 percent / Et3N / CH2Cl2 / 0.75 h / -78 °C
11: 76 percent / Li2CO3 / dimethylformamide / 5 h / 55 °C
12: 97 percent / (NH4)6Mo7O24; aq. H2O2 / aq. ethanol / 6 h / 20 °C
13: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating
14: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C
15: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C
16: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C
View Scheme

: 827325-56-4
C28H38O4

: 30220-46-3
ingenol

Conditions

Conditions	Yield
Multi-step reaction with 17 steps 1.1: PPh3; imidazole; I2 / tetrahydrofuran / 3 h / 0 °C 1.2: 94 percent / t-BuOK / tetrahydrofuran; dimethylsulfoxide / 20 °C 2.1: 49 percent / SeO2; aq. AcOH; t-BuOOH / CH2Cl2; decane / 2 h / 20 °C 3.1: 74 percent / Dess-Martin periodinane / CH2Cl2 / 1.5 h / -40 - 10 °C 4.1: 74 percent / aq. RhCl3 / aq. ethanol / 0.58 h / 115 °C 5.1: 94 percent / P(OMe)3; O2; t-BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / 0.75 h / -40 °C 6.1: 73 percent / VO(acac)2; t-BuOOH / benzene; decane / 10 h / 20 °C 7.1: 72 percent / Et3N / CH2Cl2 / 1 h / -10 - -5 °C 8.1: NaBH4 / methanol / 5 h / 20 °C 9.1: 39 mg / PPTS / CH2Cl2 / 0.5 h / Heating 10.1: 90 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 18 h / 20 °C 11.1: 96 percent / Et3N / CH2Cl2 / 0.75 h / -78 °C 12.1: 76 percent / Li2CO3 / dimethylformamide / 5 h / 55 °C 13.1: 97 percent / (NH4)6Mo7O24; aq. H2O2 / aq. ethanol / 6 h / 20 °C 14.1: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating 15.1: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C 16.1: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C 17.1: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C View Scheme

Yield

Multi-step reaction with 17 steps
1.1: PPh3; imidazole; I2 / tetrahydrofuran / 3 h / 0 °C
1.2: 94 percent / t-BuOK / tetrahydrofuran; dimethylsulfoxide / 20 °C
2.1: 49 percent / SeO2; aq. AcOH; t-BuOOH / CH2Cl2; decane / 2 h / 20 °C
3.1: 74 percent / Dess-Martin periodinane / CH2Cl2 / 1.5 h / -40 - 10 °C
4.1: 74 percent / aq. RhCl3 / aq. ethanol / 0.58 h / 115 °C
5.1: 94 percent / P(OMe)3; O2; t-BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / 0.75 h / -40 °C
6.1: 73 percent / VO(acac)2; t-BuOOH / benzene; decane / 10 h / 20 °C
7.1: 72 percent / Et3N / CH2Cl2 / 1 h / -10 - -5 °C
8.1: NaBH4 / methanol / 5 h / 20 °C
9.1: 39 mg / PPTS / CH2Cl2 / 0.5 h / Heating
10.1: 90 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 18 h / 20 °C
11.1: 96 percent / Et3N / CH2Cl2 / 0.75 h / -78 °C
12.1: 76 percent / Li2CO3 / dimethylformamide / 5 h / 55 °C
13.1: 97 percent / (NH4)6Mo7O24; aq. H2O2 / aq. ethanol / 6 h / 20 °C
14.1: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating
15.1: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C
16.1: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C
17.1: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C
View Scheme

: 827325-42-8
C28H34O5

: 30220-46-3
ingenol

Conditions

Conditions	Yield
Multi-step reaction with 12 steps 1: 73 percent / VO(acac)2; t-BuOOH / benzene; decane / 10 h / 20 °C 2: 72 percent / Et3N / CH2Cl2 / 1 h / -10 - -5 °C 3: NaBH4 / methanol / 5 h / 20 °C 4: 39 mg / PPTS / CH2Cl2 / 0.5 h / Heating 5: 90 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 18 h / 20 °C 6: 96 percent / Et3N / CH2Cl2 / 0.75 h / -78 °C 7: 76 percent / Li2CO3 / dimethylformamide / 5 h / 55 °C 8: 97 percent / (NH4)6Mo7O24; aq. H2O2 / aq. ethanol / 6 h / 20 °C 9: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating 10: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C 11: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C 12: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C View Scheme

Yield

Multi-step reaction with 12 steps
1: 73 percent / VO(acac)2; t-BuOOH / benzene; decane / 10 h / 20 °C
2: 72 percent / Et3N / CH2Cl2 / 1 h / -10 - -5 °C
3: NaBH4 / methanol / 5 h / 20 °C
4: 39 mg / PPTS / CH2Cl2 / 0.5 h / Heating
5: 90 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 18 h / 20 °C
6: 96 percent / Et3N / CH2Cl2 / 0.75 h / -78 °C
7: 76 percent / Li2CO3 / dimethylformamide / 5 h / 55 °C
8: 97 percent / (NH4)6Mo7O24; aq. H2O2 / aq. ethanol / 6 h / 20 °C
9: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating
10: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C
11: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C
12: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C
View Scheme

: 827325-51-9
C29H36O4S

: 30220-46-3
ingenol

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 97 percent / (NH4)6Mo7O24; aq. H2O2 / aq. ethanol / 6 h / 20 °C 2: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating 3: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C 4: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C 5: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C View Scheme

: 827325-40-6
C28H36O4

: 30220-46-3
ingenol

Conditions

Conditions	Yield
Multi-step reaction with 15 steps 1: 74 percent / Dess-Martin periodinane / CH2Cl2 / 1.5 h / -40 - 10 °C 2: 74 percent / aq. RhCl3 / aq. ethanol / 0.58 h / 115 °C 3: 94 percent / P(OMe)3; O2; t-BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / 0.75 h / -40 °C 4: 73 percent / VO(acac)2; t-BuOOH / benzene; decane / 10 h / 20 °C 5: 72 percent / Et3N / CH2Cl2 / 1 h / -10 - -5 °C 6: NaBH4 / methanol / 5 h / 20 °C 7: 39 mg / PPTS / CH2Cl2 / 0.5 h / Heating 8: 90 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 18 h / 20 °C 9: 96 percent / Et3N / CH2Cl2 / 0.75 h / -78 °C 10: 76 percent / Li2CO3 / dimethylformamide / 5 h / 55 °C 11: 97 percent / (NH4)6Mo7O24; aq. H2O2 / aq. ethanol / 6 h / 20 °C 12: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating 13: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C 14: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C 15: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C View Scheme

Yield

Multi-step reaction with 15 steps
1: 74 percent / Dess-Martin periodinane / CH2Cl2 / 1.5 h / -40 - 10 °C
2: 74 percent / aq. RhCl3 / aq. ethanol / 0.58 h / 115 °C
3: 94 percent / P(OMe)3; O2; t-BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / 0.75 h / -40 °C
4: 73 percent / VO(acac)2; t-BuOOH / benzene; decane / 10 h / 20 °C
5: 72 percent / Et3N / CH2Cl2 / 1 h / -10 - -5 °C
6: NaBH4 / methanol / 5 h / 20 °C
7: 39 mg / PPTS / CH2Cl2 / 0.5 h / Heating
8: 90 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 18 h / 20 °C
9: 96 percent / Et3N / CH2Cl2 / 0.75 h / -78 °C
10: 76 percent / Li2CO3 / dimethylformamide / 5 h / 55 °C
11: 97 percent / (NH4)6Mo7O24; aq. H2O2 / aq. ethanol / 6 h / 20 °C
12: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating
13: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C
14: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C
15: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C
View Scheme

: 827325-57-5
C28H34O4

: 30220-46-3
ingenol

Conditions

Conditions	Yield
Multi-step reaction with 14 steps 1: 74 percent / aq. RhCl3 / aq. ethanol / 0.58 h / 115 °C 2: 94 percent / P(OMe)3; O2; t-BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / 0.75 h / -40 °C 3: 73 percent / VO(acac)2; t-BuOOH / benzene; decane / 10 h / 20 °C 4: 72 percent / Et3N / CH2Cl2 / 1 h / -10 - -5 °C 5: NaBH4 / methanol / 5 h / 20 °C 6: 39 mg / PPTS / CH2Cl2 / 0.5 h / Heating 7: 90 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 18 h / 20 °C 8: 96 percent / Et3N / CH2Cl2 / 0.75 h / -78 °C 9: 76 percent / Li2CO3 / dimethylformamide / 5 h / 55 °C 10: 97 percent / (NH4)6Mo7O24; aq. H2O2 / aq. ethanol / 6 h / 20 °C 11: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating 12: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C 13: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C 14: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C View Scheme

Yield

Multi-step reaction with 14 steps
1: 74 percent / aq. RhCl3 / aq. ethanol / 0.58 h / 115 °C
2: 94 percent / P(OMe)3; O2; t-BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / 0.75 h / -40 °C
3: 73 percent / VO(acac)2; t-BuOOH / benzene; decane / 10 h / 20 °C
4: 72 percent / Et3N / CH2Cl2 / 1 h / -10 - -5 °C
5: NaBH4 / methanol / 5 h / 20 °C
6: 39 mg / PPTS / CH2Cl2 / 0.5 h / Heating
7: 90 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 18 h / 20 °C
8: 96 percent / Et3N / CH2Cl2 / 0.75 h / -78 °C
9: 76 percent / Li2CO3 / dimethylformamide / 5 h / 55 °C
10: 97 percent / (NH4)6Mo7O24; aq. H2O2 / aq. ethanol / 6 h / 20 °C
11: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating
12: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C
13: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C
14: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C
View Scheme

: C29H36O6S

: 30220-46-3
ingenol

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 4 h / Heating 2: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C 3: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C 4: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C View Scheme

: 827325-54-2
C29H36O6S

: 30220-46-3
ingenol

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C 2: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C 3: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C View Scheme

: 827325-52-0
C29H36O6S

: 30220-46-3
ingenol

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating 2: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C 3: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C 4: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C View Scheme

: 827325-38-2
C30H40O5

: 30220-46-3
ingenol

Conditions

Conditions	Yield
Multi-step reaction with 19 steps 1.1: aq. HCl / tetrahydrofuran / 3 h / Heating 2.1: 1.9 g / NaBH4 / ethanol; tetrahydrofuran / 0.25 h / 0 °C 3.1: PPh3; imidazole; I2 / tetrahydrofuran / 3 h / 0 °C 3.2: 94 percent / t-BuOK / tetrahydrofuran; dimethylsulfoxide / 20 °C 4.1: 49 percent / SeO2; aq. AcOH; t-BuOOH / CH2Cl2; decane / 2 h / 20 °C 5.1: 74 percent / Dess-Martin periodinane / CH2Cl2 / 1.5 h / -40 - 10 °C 6.1: 74 percent / aq. RhCl3 / aq. ethanol / 0.58 h / 115 °C 7.1: 94 percent / P(OMe)3; O2; t-BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / 0.75 h / -40 °C 8.1: 73 percent / VO(acac)2; t-BuOOH / benzene; decane / 10 h / 20 °C 9.1: 72 percent / Et3N / CH2Cl2 / 1 h / -10 - -5 °C 10.1: NaBH4 / methanol / 5 h / 20 °C 11.1: 39 mg / PPTS / CH2Cl2 / 0.5 h / Heating 12.1: 90 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 18 h / 20 °C 13.1: 96 percent / Et3N / CH2Cl2 / 0.75 h / -78 °C 14.1: 76 percent / Li2CO3 / dimethylformamide / 5 h / 55 °C 15.1: 97 percent / (NH4)6Mo7O24; aq. H2O2 / aq. ethanol / 6 h / 20 °C 16.1: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating 17.1: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C 18.1: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C 19.1: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C View Scheme

Yield

Multi-step reaction with 19 steps
1.1: aq. HCl / tetrahydrofuran / 3 h / Heating
2.1: 1.9 g / NaBH4 / ethanol; tetrahydrofuran / 0.25 h / 0 °C
3.1: PPh3; imidazole; I2 / tetrahydrofuran / 3 h / 0 °C
3.2: 94 percent / t-BuOK / tetrahydrofuran; dimethylsulfoxide / 20 °C
4.1: 49 percent / SeO2; aq. AcOH; t-BuOOH / CH2Cl2; decane / 2 h / 20 °C
5.1: 74 percent / Dess-Martin periodinane / CH2Cl2 / 1.5 h / -40 - 10 °C
6.1: 74 percent / aq. RhCl3 / aq. ethanol / 0.58 h / 115 °C
7.1: 94 percent / P(OMe)3; O2; t-BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / 0.75 h / -40 °C
8.1: 73 percent / VO(acac)2; t-BuOOH / benzene; decane / 10 h / 20 °C
9.1: 72 percent / Et3N / CH2Cl2 / 1 h / -10 - -5 °C
10.1: NaBH4 / methanol / 5 h / 20 °C
11.1: 39 mg / PPTS / CH2Cl2 / 0.5 h / Heating
12.1: 90 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 18 h / 20 °C
13.1: 96 percent / Et3N / CH2Cl2 / 0.75 h / -78 °C
14.1: 76 percent / Li2CO3 / dimethylformamide / 5 h / 55 °C
15.1: 97 percent / (NH4)6Mo7O24; aq. H2O2 / aq. ethanol / 6 h / 20 °C
16.1: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating
17.1: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C
18.1: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C
19.1: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C
View Scheme

: 827325-46-2
C28H34O6

: 30220-46-3
ingenol

Conditions

Conditions	Yield
Multi-step reaction with 11 steps 1: 72 percent / Et3N / CH2Cl2 / 1 h / -10 - -5 °C 2: NaBH4 / methanol / 5 h / 20 °C 3: 39 mg / PPTS / CH2Cl2 / 0.5 h / Heating 4: 90 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 18 h / 20 °C 5: 96 percent / Et3N / CH2Cl2 / 0.75 h / -78 °C 6: 76 percent / Li2CO3 / dimethylformamide / 5 h / 55 °C 7: 97 percent / (NH4)6Mo7O24; aq. H2O2 / aq. ethanol / 6 h / 20 °C 8: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating 9: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C 10: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C 11: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C View Scheme

Yield

Multi-step reaction with 11 steps
1: 72 percent / Et3N / CH2Cl2 / 1 h / -10 - -5 °C
2: NaBH4 / methanol / 5 h / 20 °C
3: 39 mg / PPTS / CH2Cl2 / 0.5 h / Heating
4: 90 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 18 h / 20 °C
5: 96 percent / Et3N / CH2Cl2 / 0.75 h / -78 °C
6: 76 percent / Li2CO3 / dimethylformamide / 5 h / 55 °C
7: 97 percent / (NH4)6Mo7O24; aq. H2O2 / aq. ethanol / 6 h / 20 °C
8: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating
9: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C
10: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C
11: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C
View Scheme

: 827325-48-4
C31H40O6

: 30220-46-3
ingenol

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: 90 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 18 h / 20 °C 2: 96 percent / Et3N / CH2Cl2 / 0.75 h / -78 °C 3: 76 percent / Li2CO3 / dimethylformamide / 5 h / 55 °C 4: 97 percent / (NH4)6Mo7O24; aq. H2O2 / aq. ethanol / 6 h / 20 °C 5: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating 6: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C 7: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C 8: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C View Scheme

Yield

Multi-step reaction with 8 steps
1: 90 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 18 h / 20 °C
2: 96 percent / Et3N / CH2Cl2 / 0.75 h / -78 °C
3: 76 percent / Li2CO3 / dimethylformamide / 5 h / 55 °C
4: 97 percent / (NH4)6Mo7O24; aq. H2O2 / aq. ethanol / 6 h / 20 °C
5: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating
6: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C
7: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C
8: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C
View Scheme

: C28H36O6

: 30220-46-3
ingenol

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1: 39 mg / PPTS / CH2Cl2 / 0.5 h / Heating 2: 90 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 18 h / 20 °C 3: 96 percent / Et3N / CH2Cl2 / 0.75 h / -78 °C 4: 76 percent / Li2CO3 / dimethylformamide / 5 h / 55 °C 5: 97 percent / (NH4)6Mo7O24; aq. H2O2 / aq. ethanol / 6 h / 20 °C 6: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating 7: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C 8: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C 9: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C View Scheme

Yield

Multi-step reaction with 9 steps
1: 39 mg / PPTS / CH2Cl2 / 0.5 h / Heating
2: 90 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 18 h / 20 °C
3: 96 percent / Et3N / CH2Cl2 / 0.75 h / -78 °C
4: 76 percent / Li2CO3 / dimethylformamide / 5 h / 55 °C
5: 97 percent / (NH4)6Mo7O24; aq. H2O2 / aq. ethanol / 6 h / 20 °C
6: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating
7: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C
8: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C
9: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C
View Scheme

: 30220-46-3
ingenol

: 76-83-5
trityl chloride

: 79720-52-8
ingenol 20-trityl ether

Conditions

Conditions	Yield
With pyridine Inert atmosphere;	96%
In pyridine for 24h;	89%
With dmap In pyridine for 16h; Etherification;	86%

: 30220-46-3
ingenol

: 108-24-7
acetic anhydride

: 30220-45-2
ingenol 3,5,20-triacetate

Conditions

Conditions	Yield
In pyridine	95%
With pyridine Ambient temperature; Yield given;

: 30220-46-3
ingenol

: 18162-48-6
tert-butyldimethylsilyl chloride

: Ingenol-20-(t-butyldimethylsilyl)ether

Conditions

Conditions	Yield
With 2,6-dimethylpyridine In N,N-dimethyl-formamide at 20℃; for 1.5h;	95%
In N,N-dimethyl-formamide for 0.75h;	75%

: 17217-83-3
[18O]-acetic acid

: 30220-46-3
ingenol

: 20-[18O2]-acetylingenol

Conditions

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 14h; Mitsunobu Displacement; Inert atmosphere;	92%

: 30220-46-3
ingenol

: 64-19-7
acetic acid

: 64280-37-1
ingenol monoacetate

Conditions

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; Solvent; Temperature; Reagent/catalyst; Mitsunobu Displacement; Inert atmosphere;	91%

: 30220-46-3
ingenol

: 98-88-4
benzoyl chloride

: Ingenol-3,5,20-tribenzoat

Conditions

Conditions	Yield
In pyridine	90%

: 30220-46-3
ingenol

: 107149-56-4
chlorodiethylisopropylsilane

A: (1aR,2S,5R,5aS,6S,8aS,9R,10aR)-6-((diethyl(isopropyl)silyl)oxy)-4-(((diethyl(isopropyl)silyl)oxy)methyl)-5,5a-dihydroxy-1,1,7,9-tetramethyl-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-11-one

B: (1aR,2S,5R,5aR,6S,8aS,9R,10aR)-5-((diethyl(isopropyl)silyl)oxy)-4-(((diethyl(isopropyl)silyl)oxy)methyl)-5a,6-dihydroxy-1,1,7,9-tetramethyl-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-11-one

Conditions

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 1.5h;	A 87% B 3.62%

...Expand

: 67-56-1
methanol

: 30220-46-3
ingenol

: (1aR,1bS,4R,4aS,5R,6R,7bR,8R,9aR)-3-Hydroxymethyl-6-methoxy-1,1,6,8-tetramethyl-1a,1b,4,5,6,8,9,9a-octahydro-1H-cyclopropa[3,4]benzo[1,2-e]azulene-4,4a,5,7b-tetraol

Conditions

Conditions	Yield
With perchloric acid at 20℃; for 16h; Addition; rearrangement;	84%

: 30220-46-3
ingenol

: 67-64-1
acetone

: 77573-43-4
(6S,6aR,7aR,9R,9aS,12S,12aR,12bR)-12,12a-dihydroxy-2,2,7,7,9,11-hexamethyl-4,6,6a,7,7a,8,9,12,12a,12b-decahydro-6,9a-methanocyclopenta[9,10]cyclopropa[5,6]cyclodeca[1,2-d][1,3]dioxin-13-one

Conditions

Conditions	Yield
With toluene-4-sulfonic acid at 20℃; for 1.5h; Product distribution / selectivity;	81%
With toluene-4-sulfonic acid for 0.133333h;	80%
With methanesulfonic acid In tetrahydrofuran at 45℃;	80%

: 30220-46-3
ingenol

: 67-64-1
acetone

A: 77573-43-4
(6S,6aR,7aR,9R,9aS,12S,12aR,12bR)-12,12a-dihydroxy-2,2,7,7,9,11-hexamethyl-4,6,6a,7,7a,8,9,12,12a,12b-decahydro-6,9a-methanocyclopenta[9,10]cyclopropa[5,6]cyclodeca[1,2-d][1,3]dioxin-13-one

B: Ingenol-3,4-acetonid

Conditions

Conditions	Yield
With toluene-4-sulfonic acid at 20℃; for 0.5h; Overall yield = 73 %;	A 73% B 4.5%

...Expand

: 136918-14-4
phthalimide

: 30220-46-3
ingenol

: 256427-45-9
20-deoxy-20-phthalimidoingenol

Conditions

Conditions	Yield
With PS-triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0℃; for 2h; Substitution;	67%

: 30220-46-3
ingenol

: 103-71-9
phenyl isocyanate

: ((1aR,2S,5R,5aR,6S,8aS,9R,10aR)-5,5a,6-trihydroxy-1,1,7,9-tetramethyl-11-oxo-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-4-yl)methyl phenylcarbamate

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 2h; Acylation;	51%
In dichloromethane; N,N-dimethyl-formamide at 20℃; for 5.33h;	45.4%

: 30220-46-3
ingenol

: 24045-01-0
methyl 2-(benzo[d]thiazol-2-ylsulfonyl)acetate

: C30H35NO8S2

Conditions

Conditions	Yield
Stage #1: ingenol; methyl 2-(benzo[d]thiazol-2-ylsulfonyl)acetate With triphenylphosphine In benzene at 0℃; for 0.0833333h; Stage #2: With di-isopropyl azodicarboxylate In benzene at 0 - 20℃; for 12.5h;	51%

: 30220-46-3
ingenol

: 85272-31-7
di-tert-butylsilyl bis(trifluoromethanesulfonate)

: 1356187-16-0
ingenol-5,20-(di(tert-butyl)silylene) ether

Conditions

Conditions	Yield
With 2,6-dimethylpyridine In N,N-dimethyl-formamide at 0 - 20℃;	50%

: 94487-74-8
(Z)-2-methyl-2-butenoic anhydride

: 30220-46-3
ingenol

: 1356187-34-2
ingenol 3,20-di-angelate

Conditions

Conditions	Yield
With caesium carbonate In acetonitrile at 20℃; for 1h;	48%

: 30220-46-3
ingenol

: 18162-48-6
tert-butyldimethylsilyl chloride

: ingenol-3,20-bis((t-butyldimethyl)silyl)ether

Conditions

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide for 22h;	47%

: 30220-46-3
ingenol

: 111-36-4
n-butyl isocyanide

: ((1aR,2S,5R,5aR,6S,8aS,9R,10aR)-5,5a,6-trihydroxy-1,1,7,9-tetramethyl-11-oxo-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-4-yl)methyl butylcarbamate

Conditions

Conditions	Yield
Stage #1: ingenol; n-butyl isocyanide In dichloromethane; N,N-dimethyl-formamide at 20℃; for 3.66h; Stage #2: With triethylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 18h;	46%

: 30220-46-3
ingenol

: 65-85-0
benzoic acid

A: 83036-64-0
Ingenol-3-benzoate

B: Ingenol dibenzoate

Conditions

Conditions	Yield
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at -18℃; for 72h; Acylation;	A 42% B 18%

...Expand

: 117086-91-6
1-chlorocarbonyl-2,3-dihydroindole

: 30220-46-3
ingenol

A: ((1aR,2S,5R,5aR,6S,8aS,9R,10aR)-5,5a,6-trihydroxy-1,1,7,9-tetramethyl-11-oxo-1a,2,5,5a,6, 9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-4-yl)methyl indoline-1-carboxylate

B: (1aR,2S,5R,5aS,6S,8aS,9R,10aR)-5,5a-dihydroxy-4-(((indoline-1-carbonyl)oxy)methyl)-1,1,7,9-tetramethyl-11-oxo-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-6-yl indoline-1-carboxylate

Conditions

Conditions	Yield
With potassium carbonate In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃;	A 42% B 19%

...Expand

: 30220-46-3
ingenol

: C20H26O5

Conditions

Conditions	Yield
Stage #1: ingenol With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrabutylammomium bromide In dichloromethane at 20℃; for 0.0833333h; pH=8.6; Inert atmosphere; Stage #2: With N-chloro-succinimide In dichloromethane at 20℃; for 12h; pH=8.6; Reagent/catalyst; Solvent; pH-value; Inert atmosphere;	35%

: 30220-46-3
ingenol

: 55239-75-3
N-(4-chlorophenyl)-N-methylcarbamyl chloride

: ((1aR,2S,5R,5aR,6S,8aS,9R,10aR)-5,5a,6-trihydroxy-1,1,7,9-tetramethyl-11-oxo-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-4-yl)methyl (4-chlorophenyl)(methyl)carbamate

Conditions

Conditions	Yield
Stage #1: ingenol; N-(4-chlorophenyl)-N-methylcarbamyl chloride In N,N-dimethyl-formamide at 0℃; for 0.25h; Stage #2: With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 48h;	19.98%

: 30220-46-3
ingenol

: 69034-12-4
2-chloro-5-(trifluoromethyl)pyrimidine

: (1aR,2S,5R,5aR,6S,8aS,9R,10aR)-5,5a,6-trihydroxy-1,1,7,9-tetramethyl-4-(((5-(trifluoromethyl)pyrimidin-2-yl)oxy)methyl)-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-11-one

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 39.5h;	5%

: 30220-46-3
ingenol

: 3173-56-6
benzyl isothiocyanate

: ((1aR,2S,5R,5aR,6S,8aS,9R,10aR)-5,5a,6-trihydroxy-1,1,7,9-tetramethyl-11-oxo-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-4-yl)methyl benzylcarbamate

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃;	4.7%

Ingenol Specification

The Ingenol, with the CAS registry number 30220-46-3, is also known as AC1Q6DXY. This chemical's molecular formula is C₂₀H₂₈O₅ and molecular weight is 348.43332. Its IUPAC name is called (1aR,2S,5R,5aR,6S,8aS,9R,10aR)-5,5a,6-trihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-11-one.

Physical properties of Ingenol: (1)ACD/LogP: -1.01; (2)ACD/LogD (pH 5.5): 3; (3)ACD/LogD (pH 7.4): 3; (4)ACD/BCF (pH 5.5): 103; (5)ACD/BCF (pH 7.4): 103; (6)ACD/KOC (pH 5.5): 960; (7)ACD/KOC (pH 7.4): 960; (8)#H bond acceptors: 5; (9)#H bond donors: 4; (10)#Freely Rotating Bonds: 5; (11)Index of Refraction: 1.625; (12)Molar Refractivity: 91.992 cm³; (13)Molar Volume: 260.055 cm³; (14)Surface Tension: 62.369 dyne/cm; (15)Density: 1.34 g/cm³; (16)Flash Point: 284.654 °C; (17)Enthalpy of Vaporization: 91.764 kJ/mol; (18)Boiling Point: 523.785 °C at 760 mmHg; (19)Vapour Pressure: 0 mmHg at 25°C.

When you are using this chemical, please be cautious about it as the following:
This chemical may cause inflammation to the skin or other mucous membranes. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CC1CC2C(C2(C)C)C3C=C(C(C4(C1(C3=O)C=C(C4O)C)O)O)CO
(2)InChI: InChI=1S/C20H28O5/c1-9-7-19-10(2)5-13-14(18(13,3)4)12(17(19)24)6-11(8-21)16(23)20(19,25)15(9)22/h6-7,10,12-16,21-23,25H,5,8H2,1-4H3
(3)InChIKey: VEBVPUXQAPLADL-UHFFFAOYSA-N

Product Name

INGENOL

Synthetic route

Ingenol Specification

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