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.

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收藏

页码：11787 / 11802

页数：16

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