Total synthesis of mycothiazole, a polyketide heterocycle from marine sponges

被引：42

作者：

Sugiyama, H

Yokokawa, F

Shioiri, T ^{[1
]}

机构：

[1] Meijo Univ, Grad Sch Environm & Human Sci, Nagoya, Aichi 4688502, Japan

[2] Nagoya City Univ, Grad Sch Pharmaceut Sci, Mizuho Ku, Nagoya, Aichi 4678603, Japan

来源：

TETRAHEDRON | 2003年 / 59卷 / 34期

基金：

日本学术振兴会;

关键词：

chemical manganese dioxide; Stille coupling; aldol reaction; marine natural product; absolute configuration;

D O I：

10.1016/S0040-4020(03)01020-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Mycothiazole isolated from marine sponges has been efficiently synthesized in a convergent manner. The key reactions involve the thiazole synthesis by dehydrogenation of the thiazolidine with chemical manganese dioxide (CMD), the Stille coupling, and the Nagao asymmetric acetate aldol reaction using the chiral 1,3-thiazolidine-2-thione. This synthesis clearly established the absolute configuration of natural mycothiazole to be (R). (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：6579 / 6593

页数：15

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