Total synthesis of (±)-stemonamide and (±)-isostemonamide

被引：62
作者：
Kende, AS [1 ]
Hernando, JIM [1 ]
Milbank, JBJ [1 ]
机构：
[1] Univ Rochester, Dept Chem, Rochester, NY 14627 USA
来源：
TETRAHEDRON | 2002年 / 58卷 / 01期
关键词：
stemonamide isostemonamide; acyliminium; aldol spirocyclization; Mannich reaction;
D O I：
10.1016/S0040-4020(01)01138-3
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Two different approaches to the alkaloids stemonamide and isostemonamide using N-acyliminium chemistry are described. The approach using an aldol spirocyclization to construct the second contiguous spirocenter was successful. The total synthesis of these products was completed by 1,4-addition of an appropriate side chain, alpha -methylenation by Mannich reaction, double bond isomerization and closure of the azepine ring. (C) 2002 Elsevier Science Ltd. All rights reserved.
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页码：61 / 74
页数：14
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