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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


Reference:

Hodgson, D. M., Maxwell, C. R., Wisedale, R., Matthews, I. R., Carpenter, K. J., Dickenson, A. H. and Wonnacott, S., 2001. 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. Journal of the Chemical Society: Perkin Transactions 1

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Official URL:

http://dx.doi.org/10.1039/b107414h

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.

Details

Item Type Articles
CreatorsHodgson, D. M., Maxwell, C. R., Wisedale, R., Matthews, I. R., Carpenter, K. J., Dickenson, A. H. and Wonnacott, S.
DOI10.1039/b107414h
DepartmentsFaculty of Science > Biology & Biochemistry
RefereedYes
StatusPublished
ID Code4353

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