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

Research output: Contribution to journalArticle

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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.
LanguageEnglish
Pages3150-3158
Number of pages9
JournalJournal of the Chemical Society: Perkin Transactions 1
Issue number23
DOIs
StatusPublished - 2001

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epibatidine
Heptanes
Epoxy Compounds
Nicotinic Receptors
Isomerization
Hydrogenation
Free Radicals
Rats
Brain
Nitrogen
X rays

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

In: Journal of the Chemical Society: Perkin Transactions 1, No. 23, 2001, p. 3150-3158.

Research output: Contribution to journalArticle

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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.",
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AU - Hodgson,D M

AU - Maxwell,C R

AU - Wisedale,R

AU - Matthews,I R

AU - Carpenter,K J

AU - Dickenson,A H

AU - Wonnacott,S

PY - 2001

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