Issue 23, 2001
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

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†

David M. Hodgson,*a   Christopher R. Maxwell,a   Richard Wisedale,a   Ian R. Matthews,b   Kate J. Carpenter,c   Anthony H. Dickensonc  and  Susan Wonnacottd  

* Corresponding authors

a Dyson Perrins Laboratory, Department of Chemistry, University of Oxford, South Parks Road, Oxford, UK

b Syngenta, Jealott's Hill International Research Centre, Berkshire, UK

c Department of Pharmacology, University College London, Gower Street, London, UK

d Department of Biology and Biochemistry, University of Bath, Bath, UK

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[2.2.1]hept-5-enes 28–31. Compound 31 undergoes selective exo-face hydrogenation to give the 6-substituted 2-azabicyclo[2.2.1]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.

Graphical abstract: 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

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Article information

DOI
https://doi.org/10.1039/B107414H
Article type
Paper
Submitted
17 Aug 2001
Accepted
26 Oct 2001
First published
15 Nov 2001

J. Chem. Soc., Perkin Trans. 1, 2001, 3150-3158

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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

D. M. Hodgson, C. R. Maxwell, R. Wisedale, I. R. Matthews, K. J. Carpenter, A. H. Dickenson and S. Wonnacott, J. Chem. Soc., Perkin Trans. 1, 2001, 3150 DOI: 10.1039/B107414H

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