Enantioselective synthesis of dual 5-HT4/5-HT3 serotonergic azanoradamantane SC-52491

被引：13
|
作者：
Becker, DP
Husa, RK
Moormann, AE
Villamil, CI
Flynn, DL
机构：
[1] Searle Res & Dev, Dept Med Chem, Skokie, IL 60077 USA
[2] Searle Res & Dev, Dept Med Chem, St Louis, MO 63198 USA
来源：
TETRAHEDRON | 1999年 / 55卷 / 40期
关键词：
asymmetric synthesis; Diels-Alder; serotonin; 5-hydroxytryptamine; 5-HT; azanoradamantane;
D O I：
10.1016/S0040-4020(99)00680-8
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A racemic synthesis of azanoradamantane (+/-)-3 was accomplished via Yamamoto's MAD-catalyzed Diels-Alder protocol. Subsequently, a scalable asymmetric synthesis of azanoradamantane benzamide SC-52491 was carried out employing Helmchen's asymmetric Diels-Alder methodology to construct all four contiguous asymmetric centers with the correct relative stereochemistry and in 99.3% e.e. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：11787 / 11802
页数：16
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