Enantioselective total synthesis and absolute stereostructure of hippospongic acid A

被引：24

作者：

Hioki, H

Ooi, H

Hamano, M

Mimura, Y

Yoshio, S

Kodama, M

Ohta, S

Yanai, M

Ikegami, S

机构：

[1] Tokushima Bunri Univ, Fac Pharmaceut Sci, Tokushima 7708514, Japan

[2] Hiroshima Univ, Instrument Ctr Chem Anal, Higashihiroshima 7398526, Japan

[3] Hiroshima Univ, Dept Appl Biochem, Higashihiroshima 7398528, Japan

来源：

TETRAHEDRON | 2001年 / 57卷 / 07期

关键词：

enantioselective synthesis; baker's yeast reduction; triterpene ether; gastrulation inhibitory activity; absolute stereostructure;

D O I：

10.1016/S0040-4020(00)01129-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A compound having the structure proposed for hippospongic acid A, a triterpene that specifically inhibits gastrulation of starfish embryos, was synthesized enantioselectively. The synthetic compound was not identical to the natural product. Comparison of the NMR spectra of the natural and synthetic compounds led us to propose an alternative structure, which was confirmed by enantioselective synthesis. The present synthesis established that the natural product has the (R)-configuration. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：1235 / 1246

页数：12

共 19 条

[1]

COREY EJ, 1972, TETRAHEDRON LETT, P4339

[2] Revised structure, synthesis and absolute configuration of hippospongic acid A [J].