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Towards the total synthesis of Macrolactin A. New gold(III)-catalyzed substitutions of propargylic alcohols.

Georgy, Marie (2006) Towards the total synthesis of Macrolactin A. New gold(III)-catalyzed substitutions of propargylic alcohols. PhD thesis ICSN, ICSN Institut de Chimie des Substances Naturelles, EP/X p.258.

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Alternative Locations: http://www.imprimerie.polytechnique.fr/Theses/Files/Georgy.pdf

Abstract

The first part of this thesis describes a synthetical approach of antimicrobial agent Macrolactin A. This approaoch is based on two original stratégies to build the conjugated systems: one is the isomerisation of a propagylic ketone and the other is a two reaction sequence, namely a Johnson-Claisen reaction followed by an alumina- promoted isomerisation. The stereogenic centres were built by catalytic asymmetric reactions.
The second part of the manuscript describes a new nucleophilic substitution of propargylic alcohols catalyzed by a gold(III) complex.

Item Type:PhD Thesis (PhD)
Thesis Supervisor:Campagne, Jean-Marc
Date:November 2006
Board of examiners:Joëlle, Prunet and Françoise, Colobert and Jean, Rodriguez and Hervé, Bouchard and Jean-Marc, Campagne
Ecole Doctorale:ED 447 ECOLE DOCTORALE DE L'ECOLE POLYTECHNIQUE
Discipline:ICSN
Collection (Fonds):EP/X
Institution:EP/X
Department:ICSN Institut de Chimie des Substances Naturelles
Subjects:6. Chemistry, Physical Chemistry and Chemical Engineering
Uncontrolled Keywords:Macrolactine, Antimicrobial, Asymmetric synthesis, Johnson-Claisen, Calatysis, Gold, Macrolactine, Antibiotique, Synthèse asymétrique, Johnson-Claisen, Catalyse, Or
ID Code:2171
Deposited By:Laurence Vidament
Deposited On:14 February 2007

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