Total synthesis of callystatin A, a potent cytotoxic polyketide from the marine sponge, Callyspongia truncata

被引：69

作者：

Murakami, N ^{[1
]}

Wang, WQ ^{[1
]}

Aoki, M ^{[1
]}

Tsutsui, Y ^{[1
]}

Sugimoto, M ^{[1
]}

Kobayashi, M ^{[1
]}

机构：

[1] Osaka Univ, Fac Pharmaceut Sci, Suita, Osaka 565, Japan

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 16期

关键词：

D O I：

10.1016/S0040-4039(98)00151-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A first total synthesis of callystatin A (1), a potent cytotoxic polyketide from the marine sponge Callyspongia truncata, has been achieved by use of an E-selective Wittig olefination and asymmetric Evans aldol condensation as the key reactions. Thus, the absolute stereostructure of 1 previously established by us was confirmed. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：2349 / 2352

页数：4

共 9 条

[1]

BASHA A, 1977, TETRAHEDRON LETT, P4171

[2] Determination of the relative and absolute stereochemistry of fostriecin (CI-920) [J].

Boger, DL ;

Hikota, M ;

Lewis, BM .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (06) :1748-1753

[3] A PRACTICAL ROUTE TOWARDS ALPHA,BETA-UNSATURATED DELTA-LACTONES BASED ON A [3+3] STRATEGY - SYNTHESIS OF (-)-ARGENTILACTONE [J].

CARRETERO, JC ;

GHOSEZ, L .

TETRAHEDRON LETTERS, 1988, 29 (17) :2059-2062

[4] TOTAL SYNTHESIS OF THE POLYETHER ANTIBIOTIC X-206 [J].

EVANS, DA ;

BENDER, SL ;

MORRIS, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (08) :2506-2526

[5] ENANTIOSELECTIVE ALDOL CONDENSATIONS .2. ERYTHRO-SELECTIVE CHIRAL ALOL CONDENSATIONS VIA BORON ENOLATES [J].

EVANS, DA ;

BARTROLI, J ;

SHIH, TL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (08) :2127-2129

[6] Callystatin A, a potent cytotoxic polyketide from the marine sponge, Callyspongia truncata [J].

Kobayashi, M ;

Higuchi, K ;

Murakami, N ;

Tajima, H ;

Aoki, S .

TETRAHEDRON LETTERS, 1997, 38 (16) :2859-2862

[7] Absolute stereostructure of callystatin A, a potent cytotoxic polyketide from the marine sponge, Callyspongia truncata [J].

Murakami, N ;

Wang, WQ ;

Aoki, M ;

Tsutsui, Y ;

Higuchi, K ;

Aoki, S ;

Kobayashi, M .

TETRAHEDRON LETTERS, 1997, 38 (31) :5533-5536

[8] STEREOSELECTIVE-E AND STEREOSELECTIVE-Z OLEFIN FORMATION BY WITTIG OLEFINATION OF ALDEHYDES WITH ALLYLIC PHOSPHORUS YLIDES - STEREOCHEMISTRY [J].

TAMURA, R ;

SAEGUSA, K ;

KAKIHANA, M ;

ODA, D .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (12) :2723-2728

[9]

TSUBUKI M, 1993, HETEROCYCLES, V35, P281

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