Synthesis of the CD ring in taxol from (S)-(+)-carvone

被引：9

作者：

Shing, TKM ^{[1
]}

Lee, CM ^{[1
]}

Lo, HY ^{[1
]}

机构：

[1] Chinese Univ Hong Kong, Dept Chem, Hong Kong, Peoples R China

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 47期

关键词：

taxoids; hydroxylation; Baeyer-Villiger reactions; Grignard reactions;

D O I：

10.1016/S0040-4039(01)01802-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The tricycle 16 containing a functionalized CD ring is constructed from (S)-(+)-carvone in 21 steps involving a Baeyer-Villiger oxidation, an Oppenaurer oxidation and Meerwein-Ponndorf-Verley reduction, a stereospecific Grignard addition, and an intramolecular S(N)2 reaction as the key steps. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：8361 / 8363

页数：3

共 19 条

[1] SELECTIVE HYDROLYSIS OF ALPHA,BETA-UNSATURATED AND BETA,GAMMA-UNSATURATED KETALS - METHOD FOR DECONJUGATION OF BETA,BETA-DISUBSTITUTED ALPHA,BETA-UNSATURATED KETONES [J].

BABLER, JH ;

MALEK, NC ;

COGHLAN, MJ .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (09) :1821-1823

[2] EPOXIDATION OF ALKENES BY DIOXIRANE INTERMEDIATES GENERATED IN THE REACTION OF POTASSIUM CAROATE WITH KETONES [J].

CURCI, R ;

FIORENTINO, M ;

TROISI, L ;

EDWARDS, JO ;

PATER, RH .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (23) :4758-4760

[3] 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

[4] MEERWEIN-PONNDORF-VERLEY REDUCTIONS AND OPPENAUER OXIDATIONS - AN INTEGRATED APPROACH [J].

DEGRAAUW, CF ;

PETERS, JA ;

VANBEKKUM, H ;

HUSKENS, J .

SYNTHESIS-STUTTGART, 1994, (10) :1007-1017

[5]

Donnell C. J. O., 1998, J ORG CHEM, V63, P8614

[6] 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

[7] ASYMMETRIC DIHYDROXYLATION VIA LIGAND-ACCELERATED CATALYSIS [J].

JACOBSEN, EN ;

MARKO, I ;

MUNGALL, WS ;

SCHRODER, G ;

SHARPLESS, KB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (06) :1968-1970

[8] Taxol, a molecule for all seasons [J].

Kingston, DGI .

CHEMICAL COMMUNICATIONS, 2001, (10) :867-880

[9] Enantioselective total synthesis of (-)-taxol [J].

Kusama, H ;

Hara, R ;

Kawahara, S ;

Nishimori, T ;

Kashima, H ;

Nakamura, N ;

Morihira, K ;

Kuwajima, I .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (16) :3811-3820

[10] PHEROMONE SYNTHESIS .2. PREPARATION OF PINE SAWFLY (HYMENOPTERA-DIPRIONIDAE) SEX ATTRACTANTS AND ANALOGS WITH POSSIBLE BIOLOGICAL-ACTIVITY [J].

MAGNUSSON, G .

TETRAHEDRON, 1978, 34 (09) :1385-1388

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