Asymmetric synthesis of conformationally constrained 4-hydroxyprolines and their applications to the formal synthesis of (+)-epibatidine

被引：27

作者：

Avenoza, A ^{[1
]}

Cativiela, C

Fernández-Recio, MA

Peregrina, JM

机构：

[1] Univ La Rioja, Dept Quim Quim Organ, Logrono 26001, Spain

[2] Univ Zaragoza, CSIC, Inst Ciencia Mat Aragon, Dept Quim Organ, E-50009 Zaragoza, Spain

来源：

TETRAHEDRON-ASYMMETRY | 1999年 / 10卷 / 20期

关键词：

D O I：

10.1016/S0957-4166(99)00408-5

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

This report describes the synthesis of enantiomerically pure (1S,3S,4R)- and (1S,3R,4R)-3-hydroxy-7-azabicyclo[2.2.1]heptane-1-carboxylic acids, two new conformationally constrained 4-hydroxyprolines, using a straightforward synthetic route and starting from (-)-8-phenylmenthyl 2-acetamidoacrylate. The easy transformation of the pure (1S,3S,4R)-3-hydroxy-7-azabicyclo[2.2.1] acid into (1R,4S)-N-Boc-7-azabicyclo[2.2.1]heptan-2-one constitutes a new formal synthesis of (+)-epibatidine. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：3999 / 4007

页数：9

共 46 条

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