Synthetic studies on apoptolidin: synthesis of the C12-C28 fragment via a highly stereoselective aldol reaction

被引:19
作者
Abe, K [1 ]
Kato, K [1 ]
Arai, T [1 ]
Rahim, MA [1 ]
Sultana, I [1 ]
Matsumura, S [1 ]
Toshima, K [1 ]
机构
[1] Keio Univ, Fac Sci & Technol, Dept Appl Chem, Kohoku Ku, Yokohama, Kanagawa 2238522, Japan
基金
日本学术振兴会;
关键词
apoptolidin; macrolide; antibiotic; apoptosis; aldol reaction;
D O I
10.1016/j.tetlet.2004.09.177
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The stereoselective and convergent synthesis of the C12-C28 segment 2 of the apoptosis inducing macrolide antibiotic, apoptolidin (1), is described. The synthesis involves a highly stereoselective tin(II)-mediated aldol reaction between the C17-C22 ethyl ketone 3 and the C23-C28 aldehyde 4 as the key step. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:8849 / 8853
页数:5
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