Highly stereoselective radical cyclization of haloacetals controlled by the acetal center

被引：53

作者：

Villar, M

Kolly-Kovac, T

Equey, O

Renaud, P ^{[1
]}

机构：

[1] Univ Fribourg, Dept Chem, CH-1700 Fribourg, Switzerland

[2] Univ Bern, Dept Chem & Biochem, CH-3000 Bern, Switzerland

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2003年 / 9卷 / 07期

关键词：

asymmetric synthesis; cyclizations; haloacetals; lactones; radical reactions;

D O I：

10.1002/chem.200390180

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A systematic investigation of radical haloacetal cyclizations (Ueno-Stork reaction) where the acetal center is the unique stereogenic element is reported. This highly diastereoselective reaction can be used for the preparation of polysubstituted tetrahydrofurans and gamma-lactones. We report herein the full experimental details of reactions where up to three new chiral centers are created. To demonstrate the potential of this approach, short syntheses of (+)eldanolide and of tricyclic acetals related to biologically active lignans have been achieved.

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页码：1566 / 1577

页数：12

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