Asymmetric total synthesis of Taxol(R)

被引：91

作者：

Mukaiyama, T

Shiina, I

Iwadare, H

Sakoh, H

Tani, Y

Hasegawa, M

Saitoh, K

机构：

[1] Department of Applied Chemistry, Faculty of Science, University of Tokyo, Kagurazaka, Shinjuku-ku

来源：

PROCEEDINGS OF THE JAPAN ACADEMY SERIES B-PHYSICAL AND BIOLOGICAL SCIENCES | 1997年 / 73卷 / 06期

关键词：

Taxol; 8-demethyltaxoids; 8-membered ring compounds; intramolecular aldol reaction; intramolecular pinacol cyclization; oxetane formation; dehydration;

D O I：

10.2183/pjab.73.95

中图分类号：

O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];

学科分类号：

07 ; 0710 ; 09 ;

摘要：

Asymmetric total syntheses of Taxol and of 8-demethyltaxoids 24-27 from the 8-membered ring compounds 29 and 12 respectively were completed via successive formation of the BC ring system by intramolecular aldol reaction, then the ABC ring system utilizing an intramolecular pinacol cyclization. The conversion of the tricyclic compound 43 to 7-TES baccatin III (49) was carried out by way of a newly devised method of constructing the oxetane ring. The dehydration condensation between a derivative of N-benzoylphenylisoserine and 49, followed by deprotection afforded the antitumor agent Taxol.

引用

页码：95 / 100

页数：6

共 19 条

[1] Total synthesis of baccatin III and taxol [J].

Danishefsky, SJ ;

Masters, JJ ;

Young, WB ;

Link, JT ;

Snyder, LB ;

Magee, TV ;

Jung, DK ;

Isaacs, RCA ;

Bornmann, WG ;

Alaimo, CA ;

Coburn, CA ;

DiGrandi, MJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (12) :2843-2859

[2] FIRST TOTAL SYNTHESIS OF TAXOL .1. FUNCTIONALIZATION OF THE B-RING [J].

HOLTON, RA ;

SOMOZA, C ;

KIM, HB ;

LIANG, F ;

BIEDIGER, RJ ;

BOATMAN, PD ;

SHINDO, M ;

SMITH, CC ;

KIM, SC ;

NADIZADEH, H ;

SUZUKI, Y ;

TAO, CL ;

VU, P ;

TANG, SH ;

ZHANG, PS ;

MURTHI, KK ;

GENTILE, LN ;

LIU, JH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (04) :1597-1598

[3] FIRST TOTAL SYNTHESIS OF TAXOL .2. COMPLETION OF THE C-RING AND D-RING [J].

HOLTON, RA ;

KIM, HB ;

SOMOZA, C ;

LIANG, F ;

BIEDIGER, RJ ;

BOATMAN, PD ;

SHINDO, M ;

SMITH, CC ;

KIM, SC ;

NADIZADEH, H ;

SUZUKI, Y ;

TAO, CL ;

VU, P ;

TANG, SH ;

ZHANG, PS ;

MURTHI, KK ;

GENTILE, LN ;

LIU, JH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (04) :1599-1600

[4] REACTIONS OF TERT-BUTYL PERESTERS .1. THE REACTION OF PERESTERS WITH OLEFINS [J].

KHARASCH, MS ;

SOSNOVSKY, G ;

YANG, NC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (21) :5819-5824

[5] A TOTAL SYNTHESIS OF TAXOL [J].

MASTERS, JJ ;

LINK, JT ;

SNYDER, LB ;

YOUNG, WB ;

DANISHEFSKY, SJ .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (16) :1723-1726

[6] SYNTHESIS OF AB RING MODEL SYSTEM OF TAXOL VIA ALLYLATION OF 8-MEMBERED RING COMPOUND AND INTRAMOLECULAR ALDOL CONDENSATION [J].

MUKAIYAMA, T ;

SHIINA, I ;

KIMURA, K ;

AKIYAMA, Y ;

IWADARE, H .

CHEMISTRY LETTERS, 1995, (03) :229-230

[7] A NOVEL-APPROACH TO THE SYNTHESIS OF TAXOL - A SYNTHESIS OF OPTICALLY-ACTIVE 3,7-DIBENZYLOXY-4,8-DI-T-BUTYL-DIMETHYLSILOXY-5,5-DIMETHYL-6-P-METHOXYBENZYLOXY-2-OCTANONE BY WAY OF STEREOSELECTIVE ALDOL REACTIONS [J].

MUKAIYAMA, T ;

SHIINA, I ;

SAKATA, K ;

EMURA, T ;

SETO, K ;

SAITOH, M .

CHEMISTRY LETTERS, 1995, (03) :179-180

[8] An asymmetric synthesis of the BC ring system of 8-epitaxoids by way of intramolecular aldol and successive stereoselective methylation reactions [J].

Mukaiyama, T ;

Shiina, I ;

Iwadare, H ;

Saitoh, M ;

Nishimura, K ;

Nishimura, T ;

Ohkawa, N ;

Sakoh, H ;

Saitoh, K .

CHEMISTRY LETTERS, 1996, (06) :483-484

[9] TOTAL SYNTHESIS OF TAXOL .2. CONSTRUCTION OF A-RING AND C-RING INTERMEDIATES AND INITIAL ATTEMPTS TO CONSTRUCT THE ABC RING-SYSTEM [J].

NICOLAOU, KC ;

LIU, JJ ;

YANG, Z ;

UENO, H ;

SORENSEN, EJ ;

CLAIBORNE, CF ;

GUY, RK ;

HWANG, CK ;

NAKADA, M ;

NANTERMET, PG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (02) :634-644

[10] TOTAL SYNTHESIS OF TAXOL .3. FORMATION OF TAXOLS ABC RING SKELETON [J].

NICOLAOU, KC ;

YANG, Z ;

LIU, JJ ;

NANTERMET, PG ;

CLAIBORNE, CF ;

RENAUD, J ;

GUY, RK ;

SHIBAYAMA, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (02) :645-652

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