Efficient synthesis of (+/-)-N-BOC-exo-2-(methoxycarbonyl)-7-azabicyclo[2.2.1]heptane, a versatile intermediate for the synthesis of epibatidine and epiboxidine

被引：24

作者：

Singh, S

Basmadjian, GP

机构：

[1] Dept. of Med. Chem. and Pharmaceut., Univ. of Oklahoma Hlth. Sci. Center, Oklahoma City

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 39期

关键词：

D O I：

10.1016/S0040-4039(97)01606-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-BOC-exo-2-(methoxycarbonyl)-7-azabicyclo [2.2.1]heptane, an important intermediate for the synthesis of epibatidine and its analogs was efficiently synthesized from N-BOC-exo-2-(methoxycarbonyl)-7-azabicyclo[2.2.1]hepta-2,5-diene (5) via hydrogenation followed by reductive dehalogenation or via hydrodehalogenation followed by epimerization. The diene 5 was obtained by Diels-Alder reaction. (C) 1997 Elsevier Science Ltd.

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页码：6829 / 6830

页数：2

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