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RESINIFERATOXIN CAS:57444-62-9 Qingdao Belugas Import and Export Co., Ltd. is a scientific and technological company integrating research and development, production and trade of chemical intermediates, specializing in high quality organic intermed
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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[
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Zibo Hangyu Biotechnology Development Co., Ltd
Zibo Hangyu Biotechnology Development Co., Ltd is a leading manufacturer and supplier of chemicals in China. We develop produce and distribute high quality pharmaceuticals, intermediates, special chemicals and OLED intermediates and other fine chemi
Resiniferatoxin CAS NO.57444-62-9
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Resiniferatoxin
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KAISA GROUP INC
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Hebei Mojin Biotechnology Co.,Ltd
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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[
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Acmec Resiniferatoxin 5mg
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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[
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Ansciep Chemical is a professional enterprise manufacturing and distributing fine chemicals and speciality chemicals. We have been dedicated to heterocycle compounds and phenyl rings for tens of years. This is our mature product for export. Our quali
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1,Best Quality: Our products have exported to Germany, Spain, UK, USA, Australia, Middle East, and so on other countries, and we have got very good feedback from our customers.so
Synthetic route
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1344662-01-6
2-(4-((tert-butyldimethylsilyl)oxy)-3-methoxyphenyl)acetic acid
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57444-62-9
resiniferatoxin
Conditions
| Conditions | Yield |
|---|---|
| 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% |
Conditions
| Conditions | Yield |
|---|---|
| With di-tert-butyl-diazodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 1h; Mitsunobu reaction; | 67% |
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57444-62-9
resiniferatoxin
Conditions
| Conditions | Yield |
|---|---|
| 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 |
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57444-62-9
resiniferatoxin
Conditions
| Conditions | Yield |
|---|---|
| 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 |
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57444-62-9
resiniferatoxin
Conditions
| Conditions | Yield |
|---|---|
| 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 |
-
-
57444-62-9
resiniferatoxin
Conditions
| Conditions | Yield |
|---|---|
| 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 |
-
-
57444-62-9
resiniferatoxin
Conditions
| Conditions | Yield |
|---|---|
| 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 |
-
-
57444-62-9
resiniferatoxin
Conditions
| Conditions | Yield |
|---|---|
| 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 |
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306-08-1
Homovanillic acid
-
-
57444-62-9
resiniferatoxin
Conditions
| Conditions | Yield |
|---|---|
| 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 |
-
-
57444-62-9
resiniferatoxin
Conditions
| Conditions | Yield |
|---|---|
| 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 |
-
-
57444-62-9
resiniferatoxin
Conditions
| Conditions | Yield |
|---|---|
| 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 |
-
-
57444-62-9
resiniferatoxin
Conditions
| Conditions | Yield |
|---|---|
| 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 |
-
-
57444-62-9
resiniferatoxin
Conditions
| Conditions | Yield |
|---|---|
| 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 |
-
-
57444-62-9
resiniferatoxin
Conditions
| Conditions | Yield |
|---|---|
| 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 |
-
-
57444-62-9
resiniferatoxin
Conditions
| Conditions | Yield |
|---|---|
| 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 |
-
-
57444-62-9
resiniferatoxin
Conditions
| Conditions | Yield |
|---|---|
| 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 |
-
-
57444-62-9
resiniferatoxin
Conditions
| Conditions | Yield |
|---|---|
| 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 |
-
-
57444-62-9
resiniferatoxin
Conditions
| Conditions | Yield |
|---|---|
| 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 |
-
-
57444-62-9
resiniferatoxin
Conditions
| Conditions | Yield |
|---|---|
| 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 |
-
-
57444-62-9
resiniferatoxin
Conditions
| Conditions | Yield |
|---|---|
| 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 |
-
-
57444-62-9
resiniferatoxin
Conditions
| Conditions | Yield |
|---|---|
| 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 |
-
-
57444-62-9
resiniferatoxin
Conditions
| Conditions | Yield |
|---|---|
| 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 |
-
-
57444-62-9
resiniferatoxin
Conditions
| Conditions | Yield |
|---|---|
| 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 |
-
-
57444-62-9
resiniferatoxin
Conditions
| Conditions | Yield |
|---|---|
| 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 |
-
-
57444-62-9
resiniferatoxin
Conditions
| Conditions | Yield |
|---|---|
| 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 |
-
-
57444-62-9
resiniferatoxin
Conditions
| Conditions | Yield |
|---|---|
| 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 |
-
-
57444-62-9
resiniferatoxin
Conditions
| Conditions | Yield |
|---|---|
| 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 |
-
-
57444-62-9
resiniferatoxin
Conditions
| Conditions | Yield |
|---|---|
| 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 |
-
-
57444-62-9
resiniferatoxin
Conditions
| Conditions | Yield |
|---|---|
| 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 |
-
-
57444-62-9
resiniferatoxin
Conditions
| Conditions | Yield |
|---|---|
| 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 |
-
-
57444-62-9
resiniferatoxin
Conditions
| Conditions | Yield |
|---|---|
| With sodium tetrahydroborate In ethanol for 2h; | 60% |
-
-
57444-62-9
resiniferatoxin
Conditions
| Conditions | Yield |
|---|---|
| With sodium methylate In methanol |
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