The total synthesis of (±)-merrilactone A

被引：125

作者：

Birman, VB

Danishefsky, SJ

机构：

[1] Columbia Univ, Dept Chem, New York, NY 10027 USA

[2] Sloan Kettering Inst Canc Res, Bioorgan Chem Lab, New York, NY 10021 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2002年 / 124卷 / 10期

关键词：

D O I：

10.1021/ja012495d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The total synthesis of the title compound has been accomplished in 20 steps. The key step is a free radical cyclization of vinyl bromide 29 to afford 30. The synthesis also features an efficient Diels-Alder reaction of 2,3-dimethylmaleic anhydride with 1-(tert-butyldimethylsiloxy)-butadiene. The oxetane moiety of merrilactone A is fashioned via a Payne-like rearrangement of a hydroxyepoxide (see 2 → 1). Copyright © 2002 American Chemical Society.

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页码：2080 / 2081

页数：2

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