Nitrogen bridge homoepibatidines.: syn-6-and syn-5-(6-chloro-3-pyridyl)isoquinuclidines.

被引：28

作者：

Krow, GR ^{[1
]}

Cheung, OH

Hu, ZL

Huang, QL

Hutchinson, J

Liu, NA

Nguyen, KT

Ulrich, S

Yuan, J

Xiao, YS

Wypij, DM

Zuo, FM

Carroll, PJ

机构：

[1] Temple Univ, Dept Chem, Philadelphia, PA 19122 USA

[2] CytoMed Inc, Cambridge, MA 02139 USA

[3] Univ Penn, Dept Chem, Philadelphia, PA 19104 USA

来源：

TETRAHEDRON | 1999年 / 55卷 / 25期

关键词：

epibatidine homologs; stereocontrol; bicyclic heterocyclic compounds; amines;

D O I：

10.1016/S0040-4020(99)00411-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The N-bridge vicinal-6(6-Cl-3-pyridyl) and distal 6-(6-Cl-3-pyridyl)-2-azabicyclo[2.2.2]octane homologs of the potent nicotinic receptor agonist epibatidine have been synthesized. Key steps involve stereoselective catalytic hydrogenations of both 6- and 5-(6-Cl-3-pyridyl)-2-azabicyclo[2.2.2]oct-5-enes 12 and 17 on the face anti to the nitrogen containing bridges. The vicinal homolog appears to be a potent nicotinic agonist. (C) 1999 Elsevier Science Ltd. All rights reserved.

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收藏

页码：7747 / 7756

页数：10

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