e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Total syntheses of epothilones B and d

JC Jung, R Kache, KK Vines, YS Zheng…

Index: Journal of Organic Chemistry, , vol. 69, # 26 p. 9269 - 9284

Full Text: HTML

Citation Number: 47

Abstract

... The Journal of Organic Chemistry. ... epothilone B (2). 3a Another strategy employed an aldol reaction between aldehyde E and keto acid F to provide the C6−C7 bond of acid D, which could then undergo ring closure via macrolactonization to give epothilone B (2). 3b , c,e,j,n In ...

(-)-(3S)-3-(tert-butyldimethylsilyl)oxy-4,4-dimethyl-5-oxoheptanoic acid Structure

(-)-(3S)-3-(ter...

~%

Epothilone D Structure

Ethyl 2-methylthiazole-4-carboxylate Structure

Ethyl 2-methylt...

~%

Epothilone D Structure

Diethyl 2-methylthiazole-4-methylphosphonate Structure

Diethyl 2-methy...

~%

Epothilone D Structure

N/A Structure

~%

Epothilone D Structure

(2S,9S,6Z,10E)-2,6,10-trimethyl-11-(2-methyl-1,3-thiazol-4-yl)-9-(2-trimethylsilylethoxy)methoxyundeca-6,10-dien-1-ol Structure

(2S,9S,6Z,10E)-...

~%

Epothilone D Structure

4-(CHLOROMETHYL)-2-METHYL-1,3-THIAZOLE Structure

4-(CHLOROMETHYL...

~%

Epothilone D Structure

(-)-(2R,3S,5Z)-2-(4-methoxybenzyloxy)-6,10-dimethylundeca-5,10-dien-3-ol Structure

(-)-(2R,3S,5Z)-...

~%

Epothilone D Structure

(S,Z)-6,10-dimethyl-3-((2-(trimethylsilyl)ethoxy)methoxy)undeca-5,10-dien-2-one Structure

(S,Z)-6,10-dime...

~%

Epothilone D Structure

(2R,3S,Z)-6,10-dimethyl-3-((2-(trimethylsilyl)ethoxy)methoxy)undeca-5,10-dien-2-ol Structure

(2R,3S,Z)-6,10-...

~%

Epothilone D Structure

(2-{1-[1-(4-methoxy-benzyloxy)-ethyl]-4,8-dimethyl-nona-3,8-dienyloxymethoxy}-ethyl)-trimethyl-silane Structure

(2-{1-[1-(4-met...

~%

Epothilone D Structure

2-methyl-4-[2,6,10-trimethyl-3-(2-trimethylsilanyl-ethoxymethoxy)-undeca-1,5,10-trienyl]-thiazole Structure

2-methyl-4-[2,6...

~%

Epothilone D Structure

N/A Structure

~%

Epothilone D Structure

(3S)-3-[((tert-butyl)dimethylsilyl)oxy]-1-[(1S,5R)-10,10-dimethyl-3,3-dioxido-3-thia-4-azatricyclo[5.2.1.01.5]dec-4-yl]-4,4-dimethylheptan-1,5-dione Structure

(3S)-3-[((tert-...

~%

Epothilone D Structure

(3S,6R,7S,8S,12Z,15S,16E)-3-(tert-butyldimethylsilyloxy)-7-hydroxy-15-(2-trimethylsilylethoxymethoxy)-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxoheptadeca-12,16-dienoic acid Structure

(3S,6R,7S,8S,12...

~%

Epothilone D Structure

(3S,6R,7S,8S,12Z,15S,16E)-3-((tert-butyldimethylsilyl)oxy)-15-hydroxy-4,4,6,8,12,16-hexamethyl-17-(2-methylthiazol-4-yl)-5-oxo-7-(((2,2,2-trichloroethoxy)carbonyl)oxy)heptadeca-12,16-dienoic acid Structure

(3S,6R,7S,8S,12...

~%

Epothilone D Structure

N/A Structure

~%

Epothilone D Structure

(2-methylthiazol-4-yl)methanol Structure

(2-methylthiazo...

~%

Epothilone D Structure

(3S)-1-[(1S,5R)-10,10-dimethyl-3,3-dioxido-3-thia-4-azatricyclo[5.2.1.01.5]dec-4-yl]-3-hydroxy-4,4-dimethylheptan-1,5-dione Structure

(3S)-1-[(1S,5R)...

~%

Epothilone D Structure

4-(BROMOMETHYL)-2-METHYLTHIAZOLE Structure

4-(BROMOMETHYL)...

~%

Epothilone D Structure

Ethyl 2-methylthiazole-4-carboxylate Structure

Ethyl 2-methylt...

~%

4-(BROMOMETHYL)-2-METHYLTHIAZOLE Structure

4-(BROMOMETHYL)...

D-Camphorsulfonic acid Structure

D-Camphorsulfon...

~%

n-acetyl-(2s)-bornane 10,2-sultam Structure

n-acetyl-(2s)-b...

10-camphorsulfonyl chloride Structure

10-camphorsulfo...

~%

n-acetyl-(2s)-bornane 10,2-sultam Structure

n-acetyl-(2s)-b...

(1S)-(-)-(10-Camphorsulfonyl)imine Structure

(1S)-(-)-(10-Ca...

~%

n-acetyl-(2s)-bornane 10,2-sultam Structure

n-acetyl-(2s)-b...

2,2-dimethyl-3-oxopentanal Structure

2,2-dimethyl-3-...

~%

epothilone B Structure

Ethyl 2-methylthiazole-4-carboxylate Structure

Ethyl 2-methylt...

~%

epothilone B Structure

Diethyl 2-methylthiazole-4-methylphosphonate Structure

Diethyl 2-methy...

~%

epothilone B Structure

N/A Structure

~%

epothilone B Structure

(2S,9S,6Z,10E)-2,6,10-trimethyl-11-(2-methyl-1,3-thiazol-4-yl)-9-(2-trimethylsilylethoxy)methoxyundeca-6,10-dien-1-ol Structure

(2S,9S,6Z,10E)-...

~%

epothilone B Structure

4-(CHLOROMETHYL)-2-METHYL-1,3-THIAZOLE Structure

4-(CHLOROMETHYL...

~%

epothilone B Structure

(-)-(3S)-3-(tert-butyldimethylsilyl)oxy-4,4-dimethyl-5-oxoheptanoic acid Structure

(-)-(3S)-3-(ter...

~%

epothilone B Structure

(-)-(2R,3S,5Z)-2-(4-methoxybenzyloxy)-6,10-dimethylundeca-5,10-dien-3-ol Structure

(-)-(2R,3S,5Z)-...

~%

epothilone B Structure

(S,Z)-6,10-dimethyl-3-((2-(trimethylsilyl)ethoxy)methoxy)undeca-5,10-dien-2-one Structure

(S,Z)-6,10-dime...

~%

epothilone B Structure

(2R,3S,Z)-6,10-dimethyl-3-((2-(trimethylsilyl)ethoxy)methoxy)undeca-5,10-dien-2-ol Structure

(2R,3S,Z)-6,10-...

~%

epothilone B Structure

(2-{1-[1-(4-methoxy-benzyloxy)-ethyl]-4,8-dimethyl-nona-3,8-dienyloxymethoxy}-ethyl)-trimethyl-silane Structure

(2-{1-[1-(4-met...

~%

epothilone B Structure

2-methyl-4-[2,6,10-trimethyl-3-(2-trimethylsilanyl-ethoxymethoxy)-undeca-1,5,10-trienyl]-thiazole Structure

2-methyl-4-[2,6...

~%

epothilone B Structure

N/A Structure

~%

epothilone B Structure

(13Z,4S,7R,8S,9S,16S)-4-(tert-butyldimethylsilyloxy)-8-hydroxy-5,5,7,9,13-pentamethyl-16-[(E)-1-methyl-2-(2-methylthiazol-4-yl)vinyl]oxacyclohexadec-13-ene-2,6-dione Structure

(13Z,4S,7R,8S,9...

~%

epothilone B Structure

(3S,6R,7S,8S,12Z,15S,16E)-3-(tert-butyldimethylsilyloxy)-7-hydroxy-15-(2-trimethylsilylethoxymethoxy)-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxoheptadeca-12,16-dienoic acid Structure

(3S,6R,7S,8S,12...

~%

epothilone B Structure

N/A Structure

~%

epothilone B Structure

(2-methylthiazol-4-yl)methanol Structure

(2-methylthiazo...

~%

epothilone B Structure

(3S)-3-[((tert-butyl)dimethylsilyl)oxy]-1-[(1S,5R)-10,10-dimethyl-3,3-dioxido-3-thia-4-azatricyclo[5.2.1.01.5]dec-4-yl]-4,4-dimethylheptan-1,5-dione Structure

(3S)-3-[((tert-...

~%

epothilone B Structure

(3S)-1-[(1S,5R)-10,10-dimethyl-3,3-dioxido-3-thia-4-azatricyclo[5.2.1.01.5]dec-4-yl]-3-hydroxy-4,4-dimethylheptan-1,5-dione Structure

(3S)-1-[(1S,5R)...

~%

epothilone B Structure

(3S,6R,7S,8S,12Z,15S,16E)-3-((tert-butyldimethylsilyl)oxy)-15-hydroxy-4,4,6,8,12,16-hexamethyl-17-(2-methylthiazol-4-yl)-5-oxo-7-(((2,2,2-trichloroethoxy)carbonyl)oxy)heptadeca-12,16-dienoic acid Structure

(3S,6R,7S,8S,12...

~%

epothilone B Structure

4-(BROMOMETHYL)-2-METHYLTHIAZOLE Structure

4-(BROMOMETHYL)...

~%

epothilone B Structure

D-Camphorsulfonic acid Structure

D-Camphorsulfon...

~%

(2R)-Bornane-10,2-sultam Structure

(2R)-Bornane-10...

10-camphorsulfonyl chloride Structure

10-camphorsulfo...

~%

(2R)-Bornane-10,2-sultam Structure

(2R)-Bornane-10...

2,2-dimethyl-3-oxopentanal Structure

2,2-dimethyl-3-...

~%

Epothilone D Structure

Total syntheses of epothilones A and B

[Journal of the American Chemical Society, , vol. 119, # 42 p. 10073 - 10092]

Complex target-oriented total synthesis in the drug discover...

[Journal of the American Chemical Society, , vol. 125, # 10 p. 2899 - 2901]

Complex target-oriented total synthesis in the drug discover...

[Journal of the American Chemical Society, , vol. 125, # 10 p. 2899 - 2901]

Complex target-oriented total synthesis in the drug discover...

[Journal of the American Chemical Society, , vol. 125, # 10 p. 2899 - 2901]

Complex target-oriented total synthesis in the drug discover...

[Journal of the American Chemical Society, , vol. 125, # 10 p. 2899 - 2901]