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

1999; Elsevier BV; Volume: 55; Issue: 25 Linguagem: Inglês

10.1016/s0040-4020(99)00411-1

1464-5416

Grant R. Krow, Osbert H. Cheung, Zilun Hu, Qiuli Huang, John P. Hutchinson, Nian Liu, Kevin T. Nguyen, Scott M. Ulrich, Jing Yuan, Yushi Xiao, Donna M. Wypij, Fangming Zuo, Patrick J. Carroll,

Chemical synthesis and alkaloids

Abstract 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 stereo-selective 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.