Spongistatin synthetic studies. An efficient, second-generation construction of an advanced ABCD intermediate

被引：86
|
作者：
Smith, AB [1 ]
Doughty, VA [1 ]
Sfouggatakis, C [1 ]
Bennett, CS [1 ]
Koyanagi, J [1 ]
Takeuchi, M [1 ]
机构：
[1] Univ Penn, Dept Chem, Philadelphia, PA 19104 USA
来源：
ORGANIC LETTERS | 2002年 / 4卷 / 05期
关键词：
D O I：
10.1021/ol017273z
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
[GRAPHICS] A short, efficient, and stereocontrolled synthesis of (-)-4, an advanced ABCD subunit of the spongistatins, has been achieved. Central to the synthetic strategy is the multicomponent linchpin union of silyl dithianes with epoxides to access both the AB and CD fragments. Fragment coupling was then achieved via an efficient stereoselective aldol reaction. The linear sequence required 22 steps and proceeded in 4.0% overall yield.
引用
收藏
页码：783 / 786
页数：4
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