A highly stereoselective asymmetric synthesis of (--)-lobeline and (--)-sedamine.

Full 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.

Author information

Author/s: Felpin, François-Xavier (FX); Lebreton, Jacques (J);

Affiliation: Laboratoire de Synthèse Organique, Faculté des Sciences et des Techniques, CNRS UMR 6513, 2 rue de la Houssinière, BP 92208, 44322 Nantes Cedex 3, France.

Journal and publication information

Publication Type: Journal Article; Research Support, Non-U.S. Gov't

Journal: The Journal of organic chemistry (J Org Chem), published in United States. (Language: eng)

Reference: 2002-Dec; vol 67 (issue 26) : pp 9192-9

Dates: Created 2002/12/20; Completed 2003/05/29; Revised 2006/11/15;

PMID: 12492320, status: MEDLINE (last retrieval date: 2/18/2009, IMS Date: )

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