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Paper | Regular issue | Vol 55, No. 9, 2001, pp.1689-1701
Published online, 1st January, 1970
DOI: 10.3987/COM-01-9255
Diastereoselective Reduction of Chiral Enaminolactones: A Short and Convenient Route to Enantio-pure (+)-Tashiromine

Olivier David, Christian Bellec, Marie-Claude Fargeau-Bellassoued, and Gérard Lhommet*

*Laboratoire de Chimie des Hétérocycles UMR 7611, Université P. et M. Curie, case courrier 43, 4 Place Jussieu, F-75252 Paris Cedex 05, France


Some chiral β-enamino lactones were reduced catalytically or chemically with good to moderate diastereoselectivity owing to a chiral induction originated from (S)-α-methylbenzylamine. The scope of the present methodology has been extended to the synthesis of an indolizidine alkaloid : (+)-tashiromine. A synthesis of this natural product was achieved in a short and attractive manner (five steps from thiolactam) to enantiopure alkaloid in 25 % overall yield.