A versatile and stereoselective synthesis of (rac)-epibatidine
- Avenoza, A. 1
- Busto, J.H. 1
- Cativiela, C. 2
- Peregrina, J.M. 1
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1
Universidad de La Rioja
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2
Instituto de Nanociencia y Materiales de Aragón
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ISSN: 0039-7881
Year of publication: 1998
Volume: 9
Pages: 1335-1338
Type: Article
More publications in: Synthesis (Stuttgart)
Abstract
A new synthesis of (±)-epibatidine has been achieved, involving a Diels-Alder cycloaddition of (Z)-4-[5'-(2'-chloropyridylmethylene)]-2-phenyl-5(4H)-oxazolone with Danishefsky's diene, and an intramolecular nucleophilic displacement in a trans-1,4-methanesulfonyloxycyclohexylamide derivative as key steps.