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Synlett 1998; 1998(12): 1349-1350
DOI: 10.1055/s-1998-1963
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An Epoxide Rearrangement - Radical Rearrangement Approach to 6-Substituted 2-Azabicyclo[2.2.1]-5-heptenes: Synthesis of an Epibatidine Analogue

David M. Hodgson* , Christopher R. Maxwell, Ian R. Matthews
  • *Dyson Perrins Laboratory, Department of Chemistry, University of Oxford, South Parks Road, Oxford OX1 3QY, UK; Fax + 44 (0) 1865 275 674
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Publication Date:
31 December 2000 (online)

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Base-induced isomerisation of epoxide 9 gives an azanortricyclanol 10 which is a precursor for a novel free-radical induced rearrangement to 6-substituted 2-azabicyclo[2.2.1]-5-heptenes 14 a - c; 14 c (R = 6-chloro-3-pyridinyl) is converted to the epibatidine analogue 2.

epoxide - rearrangement - radical deoxygenation - epibatidine