An enantioselective biomimetic total synthesis of (-)-siccanin

被引：83

作者：

Trost, BM ^{[1
]}

Shen, HC ^{[1
]}

Surivet, JP ^{[1
]}

机构：

[1] Stanford Univ, Dept Chem, Stanford, CA 94305 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2003年 / 42卷 / 33期

关键词：

asymmetric synthesis; biomimetic synthesis; cyclization; natural products; radical reactions;

D O I：

10.1002/anie.200351868

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A convergent asymmetric synthesis of the clinically important antifungal agent (-)-siccanin (1) mimics the proposed biosynthetic pathway. A Pd-catalyzed asymmetric allylic alkylation was used to establish the stereochemistry, and sequential radical processes (a TiIII-promoted cyclization followed by diacetoxyiodobenzene-promoted tetrahydrofuran formation) led to the completion of the first asymmetric synthesis of 1.

引用

页码：3943 / 3947

页数：5

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[2]

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[3]

BELLOTTI MG, 1985, CHEMIOTERAPIA, V4, P431

[4]

Buckle D. R., 1995, ENCY REAGENTS ORGANI, V3, P1699