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Synlett 1997; 1997(5): 589-590
DOI: 10.1055/s-1997-3225
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A Concise Stereoselective Synthesis of Epibatidine Employing Conjugate Addition to an Alkenyl Sulfone Intermediate as the Key Step

Gerrard M. P. Giblin1 , Clifford D. Jones2 , Nigel S. Simpkins3
  • 1Glaxo Wellcome, Medicines Research Centre, Gunnels Wood Road, Stevenage, Hertfordshire, SG1 2NY, England, U.K.
  • 2Department of Chemistry, The University of Nottingham, University Park, Nottingham, NG7 2RD, UK
  • 3Department of Chemistry, The University of Nottingham, University Park, Nottingham, NG7 2RD, UK, Fax (0115) 9513564; e-mail nigel.Simpkins@Nottingham.ac.uk
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Publication History

Publication Date:
31 December 2000 (online)

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A new synthesis of racemic epibatidine has been achieved, which involves conjugate addition of a metallated 2-methoxypyridine derivative to a suitably protected azabicyclic alkenyl sulfone as the key step.

epibatidine - alkaloid - cycloaddition - alkenyl sulfone