A convergent total synthesis of hemibrevetoxin B

被引：109

作者：

Zakarian, A ^{[1
]}

Batch, A ^{[1
]}

Holton, RA ^{[1
]}

机构：

[1] Florida State Univ, Dept Chem, Tallahassee, FL 32306 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2003年 / 125卷 / 26期

关键词：

D O I：

10.1021/ja029225v

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A convergent biomimetic synthesis of hemibrevetoxin B from d-glucal and d-arabinose utilizes an electrophile-promoted cascade anti-Baldwin cyclization of an epoxy alcohol. The epoxy alcohol arises from a palladium-catalyzed coupling of a highly functionalized organozinc compound and an alkenyl iodide, which serve as two chiral building blocks of similar size and complexity. This first successful implementation of a cascade epoxy alcohol cyclization for the synthesis of marine polycyclic ether toxins proceeds in 39 steps and 4% overall yield. Copyright © 2003 American Chemical Society.

引用

页码：7822 / 7824

页数：3

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