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Approches synthétiques du (+)-discodermolide et du dolabélide A par hydrogénation asymétrique à l'aide de complexes chiraux de ruthénium

Abstract : The Ocean is a large source of potential anti-cancer molecules. This manuscript describes a synthetic approach of two natural cytotoxic molecules : (+)-discodermolide and dolabelide A. The polypropionate moeties of these molecules were created using an association of three reactions : Claisen condensation to create β-ketoesters, ruthenium-catalyzed asymmetric hydrogenation of β-ketoesters then diastereoselective methylation of β-hydroxyester. Thus, three intermediate fragments of (+)-discodermolide were elaborated and 12 stereogenic centers were set out, 8 of which were installed using either asymmetric hydrogenation or diastereoselective methylation with an excellent stereoselectivity. Besides, two fully elaborated fragments of dolabelide A were prepared and 7 out of 8 hydroxyl functional groups were installed using asymmetric hydrogenation with selectivities up to 95 %.
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https://pastel.archives-ouvertes.fr/pastel-00004977
Contributor : Ecole Chimie Paristech <>
Submitted on : Monday, April 6, 2009 - 8:00:00 AM
Last modification on : Monday, April 6, 2009 - 8:00:00 AM
Long-term archiving on: : Thursday, September 30, 2010 - 8:56:24 PM

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  • HAL Id : pastel-00004977, version 1

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Christophe Roche. Approches synthétiques du (+)-discodermolide et du dolabélide A par hydrogénation asymétrique à l'aide de complexes chiraux de ruthénium. Chemical Sciences. Chimie ParisTech, 2008. English. ⟨pastel-00004977⟩

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