Expeditious formal synthesis of (±)-epibatidine using diastereoselective bromohydroxylation of aminocyclohexene derivatives

被引：62

作者：

Cabanal-Duvillard, I

Berrien, JF

Royer, J ^{[1
]}

Husson, HP

机构：

[1] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France

[2] Fac Pharm, CNRS, UMR, F-92296 Chatenay Malabry, France

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 29期

关键词：

D O I：

10.1016/S0040-4039(98)01017-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Bromination and bromohydroxylation of oxa/olidinones derived from cyclohexadiene have been studied in order to synthetize (+/-)-epibatidine 18. Bromohydroxylation of compound 2 led to a polyfunctionalized halohydrin 11a which could be further cyclized to azabicyclo[2.2.1]heptan-2-one 16 already described as a precursor of epibatidine 18. (C) 1998 Elsevier Science Ltd. All rights reserved.

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页码：5181 / 5184

页数：4

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