Dinuclear asymmetric Zn aldol additions: Formal asymmetric synthesis of fostriecin

被引：115

作者：

Trost, BM ^{[1
]}

Frederiksen, MU ^{[1
]}

Papillon, JPN ^{[1
]}

Harrington, PE ^{[1
]}

Shin, S ^{[1
]}

Shireman, BT ^{[1
]}

机构：

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

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2005年 / 127卷 / 11期

关键词：

D O I：

10.1021/ja042435i

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Direct asymmetric aldol reactions constitute a powerful methodology for the efficient synthesis of complex natural products. Herein we report the first application of our recently reported dinuclear Zn-catalyzed direct aldol addition of alkynyl ketones to aldehydes in a short and efficient formal asymmetric synthesis of fostriecin, a potent cyctotoxic natural product. This work highlights not only the power of the aldol methodology but also the utility of the akynyl silane aldol adducts, as it is subsequently utilized in a vinyl silane cross-coupling reaction which affords the target molecule in 14 steps for the longest linear sequence in 8.5% overall yield. Copyright © 2005 American Chemical Society.

引用

页码：3666 / 3667

页数：2

共 36 条

[31] Asymmetric total synthesis of (+)-fostriecin [J].