（-）-霉菌噻唑的不对称全合成。

Asymmetric total synthesis of (-)-mycothiazole.

作者信息

Sugiyama H, Yokokawa F, Shioiri T

机构信息

Faculty of Pharmaceutical Sciences, Nagoya City University, Tanabe-dori, Mizuho-ku, Nagoya 467-8603, Japan.

出版信息

Org Lett. 2000 Jul 13;2(14):2149-52. doi: 10.1021/ol000128l.

DOI:10.1021/ol000128l

PMID:10891253

Abstract

[structure: see text] In this Letter we describe the first total synthesis of mycothiazole, a polyketide thiazole from a marine sponge. Key steps include our CMD oxidation for the conversion of thiazolidine 11 to thiazole 12 and the Nagao acetate aldol reaction of 5 with aldehyde 4 to construct the chiral secondary alcohol. The skipped diene was constructed by the standard Stille coupling, and the conjugated diene was synthesized by lithium(I)- and copper(I)-mediated Stille coupling.

摘要

[结构：见正文] 在本信函中，我们描述了首次全合成来自海洋海绵的聚酮噻唑类化合物——霉菌噻唑。关键步骤包括我们用于将噻唑烷11转化为噻唑12的CMD氧化反应，以及5与醛4的长谷川乙酸酯羟醛反应以构建手性仲醇。通过标准的Stille偶联构建了跳跃二烯，通过锂（I）和铜（I）介导的Stille偶联合成了共轭二烯。