6-Substituted 2-azabicyclo[2.2.1]hept-5-enes by nitrogen-directed radical rearrangement: Synthesis of an epibatidine analogue with high binding affinity at the nicotinic acetylcholine receptor

D M Hodgson, C R Maxwell, R Wisedale, I R Matthews, K J Carpenter, A H Dickenson, S Wonnacott

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40 Citations (Scopus)

Abstract

Base-induced isomerisation of epoxide 13 gives an azanortricyclanol 17 which is a precursor for a novel free-radical induced rearrangement to 6-substituted 2-azabicyclo[2.2. I]hept-5-enes 28-31. Compound 31 undergoes selective exo-face hydrogenation to give the 6-substituted 2-azabicyclo[2.2. I]heptane 33 (structure confirmed by X-ray crystallographic analysis). Deprotection of 33 gives epibatidine analogue 2 which has been shown to bind with high affinity at rat brain nicotinic acetylcholine receptors.
Original languageEnglish
Pages (from-to)3150-3158
Number of pages9
JournalJournal of the Chemical Society: Perkin Transactions 1
Issue number23
DOIs
Publication statusPublished - 2001

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