Desymmetrization of 1,4-dien-3-ols and related compounds via Ueno-Stork radical cyclizations

被引：49

作者：

Villar, F ^{[1
]}

Equey, O ^{[1
]}

Renaud, P ^{[1
]}

机构：

[1] Univ Fribourg, Inst Chim Organ, Perolles, CH-1700 Fribourg, Switzerland

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 08期

关键词：

D O I：

10.1021/ol005613v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Desymmetrization of 1,4-dien-3-ols and related compounds via Ueno-Stork radical cyclizations is reported. The stereochemistry of the cyclization is controlled by the acetal center. Excellent stereocontrol at C(4) and C(5) of the newly formed tetrahydrofuran rings is observed. Use of a chiral auxiliary allows the preparation of enantiomerically pure material. The utility of this method has been demonstrated by achieving a short synthesis of (+)-eldanolide, the pheromone of the male African sugarcane stem borer Eldana saccharina.

引用

页码：1061 / 1064

页数：4