Asymmetric synthesis of conformationally constrained 4-hydroxyprolines and their applications to the formal synthesis of (+)-epibatidine
- Avenoza, A. 1
- Cativiela, C. 2
- Fernández-Recio, M.A. 1
- 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: 0957-4166
Année de publication: 1999
Volumen: 10
Número: 20
Pages: 3999-4007
Type: Article
beta Ver similares en nube de resultadosD'autres publications dans: Tetrahedron: Asymmetry
Résumé
This report describes the synthesis of enantiomerically pure (1S,3S,4R)- and (1S,3R,4R)-3-hydroxy-7-azabicyclo[2.2.1]heptane-1-carboxylic acids, two new conformationally constrained 4-hydroxyprolines, using a straightforward synthetic route and starting from (-)-8-phenylmenthyl 2-acetamidoacrylate. The easy transformation of the pure (1S,3S,4R)-3-hydroxy-7- azabicyclo[2.2.1]heptane-1-carboxylic acid into (1R,4S)-N-Boc-7- azabicyclo[2.2.1]heptan-2-one constitutes a new formal synthesis of (+)- epibatidine.