A stereoselective synthesis of the macrolide core of migrastatin

被引：10

作者：

Das, Parthasarathi ^{[1
]}

Saibaba, Vobbalareddy ^{[1
]}

Kumar, Chetlur Kiran ^{[1
]}

Mahendar, Velisoju ^{[1
]}

机构：

[1] Dr Reddys Labs Ltd, Discovery Res, Hyderabad 500049, Andhra Pradesh, India

来源：

SYNTHESIS-STUTTGART | 2008年 / 3卷 / 03期

关键词：

metastasis; macrolide; Evans aldol condensation; Wittig olefination; ring-closing metathesis;

D O I：

10.1055/s-2008-1032028

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A concise and efficient synthesis of the macrolide core of migrastatin, an antimetastatic agent, is reported. In this synthetic protocol, the key intermediate (4R,5S,6S)-6-methoxy-5-(4-meth-oxybenzyloxy)-2,4-dimethylocta-2,7-dien-l-ol is obtained after diastereoselective aldol condensation, Lewis acid mediated diastereoselective addition, and an exclusive Z-olefination sequence have been employed. Yamaguchi esterification of the key intermediate, followed by ring-closing metathesis produced the desired macrolide in high selectivity and good yield.

引用

页码：445 / 451

页数：7

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