HETEROCYCLES

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact: purchase@heterocycles.com

Price: ¥ 4,400 (Yen only)
Period: This Article can be accessed for 7 days.

■ 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

Abstract

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.