Total Synthesis of Epothilone D: The Nerol/Macroaldolization Approach

被引：26

作者：

Wessjohann, Ludger A. ^{[1
,2
]}

Scheid, Guenther O. ^{[1
,2
]}

Eichelberger, Uwe ^{[1
]}

Umbreen, Sumaira ^{[1
]}

机构：

[1] Leibniz Inst Plant Biochem, Dept Bioorgan Chem, D-06120 Halle, Saale, Germany

[2] Vrije Univ Amsterdam, Amsterdam, Netherlands

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 21期

关键词：

MICROTUBULE-STABILIZING AGENTS; NATURAL-PRODUCTS; ALDOL CONDENSATION; PURIFIED TUBULIN; BETA-TUBULIN; ANALOGS; TAXOL; PACLITAXEL; RESOLUTION; RESISTANT;

D O I：

10.1021/jo401355r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly convergent and stereocontrolled synthesis of epothilone D (4) is reported. Key features are a cheap and Z-selective synthesis of the northern half based on nerol and acetoacetate and chromium(II)-mediated Reformatsky reactions as a powerful tool for chemoselective asymmetric carbon-carbon bond formations, including an unusual stereospecific macroaldolization.

引用

页码：10588 / 10595

页数：8

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