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A highly stereoselective asymmetric synthesis of (--)-lobeline and (--)-sedamine
François-Xavier Felpin1, Jacques Lebreton
1Laboratoire de Synthèse Organique, Faculté des Sciences et des Techniques, CNRS UMR 6513, 2 rue de la Houssinière, BP 92208, 44322 Nantes Cedex 3, France.
The Journal of Organic Chemistry
|December 21, 2002
Abstract:
A highly stereoselective asymmetric synthesis of (--)-sedamine and (--)-lobeline is described from benzaldehyde in 16 and 17 steps with an overall yield of 20% and 14%, respectively. The key intermediate syn-3,4-epoxyalcohol was prepared in a highly diastereomeric fashion (>99% ee, dr) and served as a common intermediate for both alkaloids.