Total synthesis of (-)-laulimalide

被引：82

作者：

Wender, PA ^{[1
]}

Hegde, SG ^{[1
]}

Hubbard, RD ^{[1
]}

Zhang, L ^{[1
]}

机构：

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

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2002年 / 124卷 / 18期

关键词：

D O I：

10.1021/ja0258428

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(-)-Laulimalide (1), a structurally novel macrolide isolated in trace amounts from marine sponges, promotes abnormal tubulin polymerization and apoptosis in vitro, with a similar mode of action to that of Taxol-, but with potentially less susceptibility to multidrug resistance. Herein, a flexible and convergent asymmetric synthesis of (-)-laulimalide is described. This synthesis featured a highly diastereoselective Sakurai reaction of 2 with 3 and a regioselective macrolactonization of an unprotected vicinal diol. Laulimalide was synthesized in 25 steps (longest linear; 36 overall) in 3.5% overall yield, providing a uniquely short and efficient route to 1 and its analogues. Copyright © 2002 American Chemical Society.

引用

页码：4956 / 4957

页数：2

共 36 条

[1] INSITU CUPRATE FORMATION VIA TRANSMETALATION BETWEEN VINYLSTANNANES AND HIGHER-ORDER CYANOCUPRATES [J].