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

Resiniferatoxin Synthetic route

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

: C31H39ClO5Si

: 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%

: 306-08-1
Homovanillic acid

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

: 57444-62-9
resiniferatoxin

Conditions

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

: C17H28O5

: 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

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

: C12H20O5

: 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

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

: C19H24O6

: 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

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

: C21H24O6

: 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

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

: C24H32O6Si

: 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

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

: C15H9Cl3O3

: 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

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

: 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

: C29H38O8S4

: 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

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

Resiniferatoxin Chemical Properties

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

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

Resiniferatoxin Toxicity Data With Reference

ice-unr TDLo: 50 ng/kg

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

Resiniferatoxin Safety Profile

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

Resiniferatoxin Specification

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

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