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Synthesis 2008(17): 2771-2775  
DOI: 10.1055/s-2008-1067204
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Strategy for the Assembly of Chiral Bicyclic Lactams: A Concise Synthetic Route to (-)-Coniceine

Stéphane Lebruna,b, Axel Couture*a,b, Eric Deniaua,b, Pierre Grandclaudona,b
a Université des Sciences et Technologies de Lille 1, LCOP, Bâtiment C3(2), 59655 Villeneuve d"Ascq, France
b CNRS, UMR 8009 ‘Chimie Organique et Macromoléculaire’, 59655 Villeneuve d’Ascq, France
Fax: +33(3)20336309; e-Mail: axel.couture@univ-lille1.fr;
Further Information

Publication History

Received 23 April 2008
Publication Date:
24 July 2008 (online)

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Abstract

A concise asymmetric synthesis of chiral bicyclic lactams combining a highly stereoselective 1,2-addition on SAMP hydrazones with a ring closure metathesis has been achieved. The synthetic utility of this approach has been emphasized by the total synthesis of (-)-coniceine in high enantiomeric excess.

Key words

alkaloids - lactams - metathesis - ring closure - stereo­selectivity

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