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Diastereoselective Reduction of Bicyclic -Enamino Carbonyl Piperidines – Application to the Total Synthesis of (–)-Deoxocassine

Authors

  • Romain Noël,

    1. Université Pierre et Marie Curie-Paris 6, Laboratoire de Chimie Organique (UMR CNRS 7611), Equipe de Chimie des Hétérocycles, Institut de Chimie Moléculaire (FR 2769), 4 place Jussieu, 75252 Paris cedex 05, France, Fax: +33-1-44-27-30-56
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  • Corinne Vanucci-Bacqué,

    1. Université Pierre et Marie Curie-Paris 6, Laboratoire de Chimie Organique (UMR CNRS 7611), Equipe de Chimie des Hétérocycles, Institut de Chimie Moléculaire (FR 2769), 4 place Jussieu, 75252 Paris cedex 05, France, Fax: +33-1-44-27-30-56
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  • Marie-Claude Fargeau-Bellassoued,

    1. Université Pierre et Marie Curie-Paris 6, Laboratoire de Chimie Organique (UMR CNRS 7611), Equipe de Chimie des Hétérocycles, Institut de Chimie Moléculaire (FR 2769), 4 place Jussieu, 75252 Paris cedex 05, France, Fax: +33-1-44-27-30-56
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  • Gérard Lhommet

    1. Université Pierre et Marie Curie-Paris 6, Laboratoire de Chimie Organique (UMR CNRS 7611), Equipe de Chimie des Hétérocycles, Institut de Chimie Moléculaire (FR 2769), 4 place Jussieu, 75252 Paris cedex 05, France, Fax: +33-1-44-27-30-56
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Abstract

The chemo- and diastereoselective reduction of chiral piperidine β-enamino esters 4 and 6 and β-enamino ketones 5 and 7 was studied and found to afford 2,3- or 2,3,6-substituted piperidines. This approach was successfully applied to the total synthesis of (–)-deoxocassine. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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