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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

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.
Publication status:
Published

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Publisher copy:
10.1039/b107414h

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Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
Journal:
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 More from this journal
Issue:
23
Pages:
3150-3158
Publication date:
2001-01-01
DOI:
ISSN:
1472-7781
Language:
English
Pubs id:
pubs:38029
UUID:
uuid:ce6e5f1d-2092-446c-a407-e43ac4dfb41d
Local pid:
pubs:38029
Source identifiers:
38029
Deposit date:
2012-12-19

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