Gold(I)-catalyzed cyclizations of silyl enol ethers: Application to the synthesis of (+)-lycopladine A

被引：207

作者：

Staben, Steven T. ^{[1
]}

Kennedy-Smith, Joshua J. ^{[1
]}

Huang, David ^{[1
]}

Corkey, Britton K. ^{[1
]}

LaLonde, Rebecca L. ^{[1
]}

Toste, F. Dean ^{[1
]}

机构：

[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2006年 / 45卷 / 36期

关键词：

alkaloids; carbocyclization; gold; homogeneous catalysis; silyl enol ethers;

D O I：

10.1002/anie.200602035

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) In control: Gold(I)-catalyzed intramolecular addition of silyl enol ethers to alkynes and allenes allows for the diastereoselective synthesis of cyclopentenes with control of the position of the double bond. The utility of these reactions is demonstrated by an efficient total synthesis of (+)-lycopladine A that takes advantage of the orthogonal reactivity of AuI and Pd0 towards unsaturated iodides (see scheme). © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：5991 / 5994

页数：4

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