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Approaches to syn-7-substituted 2-azanorbornanes as potential nicotinic agonists; Synthesis of syn- and anti-isoepibatidine

By J. R. Malpass, S. Handa and R. White


Coupling of N-Boc-7-bromo-2-azabicyclo[2.2.1]heptane with aryl and pyridyl boronic acids incorporates aryl and heterocyclic substituents at the 7-position and leads to a preference for syn over anti stereoisomers. Incorporation of a chloropyridyl group followed by N-deprotection gives syn-isoepibatidine. Facial selectivity in attack on 7-keto-2-azanorbornanes depends heavily on the N-protecting group leading to the first syn-7-hydroxy-2-azabicyclo[2.2.1]heptane derivative

Year: 2005
DOI identifier: 10.1021/ol0510365
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