Enantiodivergent total syntheses of (+)- and (-)-scopadulcic acid A

被引：142

作者：

Fox, ME ^{[1
]}

Li, C ^{[1
]}

Marino, JP ^{[1
]}

Overman, LE ^{[1
]}

机构：

[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1999年 / 121卷 / 23期

关键词：

D O I：

10.1021/ja990404v

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first enantioselective total synthesis of scopadulcic acid A is described. The key step is a cascade intramolecular Heck reaction of a methylenecycloheptene iodide, which generates the B, C, and D rings of the scopadulan ring system in 90% yield as a single stereoisomer. A distinctive feature of these syntheses is the use of stereoselective enolization to dictate which enantiomer of the natural product is produced.

引用

页码：5467 / 5480

页数：14

共 72 条

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