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Approches synthétiques vers le mycothiazole-4,19-diol : utilisation du palladium en synthèse organique

Abstract : Mycothiazole-4,19-diol is a natural compound isolated in 2006 from a marine sponge cacospongia mycofijiensis which has never been synthesized. Its unique structure, its weak abundance and its potential biological activity make mycothiazole-4,19-diol an attractive target in organic chemistry. The challenge is the building of allylic diol-1,2 moiety. In order to make a concise and elegant synthesis of this molecule, four disconnections and many approaches have been studied. A study about the use of palladium in organic synthesis has also been done. Among all the catalytic systems in which this metal is involved, we were first interested in the aerobic oxidation of alcohols into their corresponding carbonyl compounds. We have elaborated a new catalytic system which enables the selective oxidation of allylic alcohols. This methodology has been applied in the different synthetic approaches towards the mycothiazole-4,19-diol. A second study has been done about the use of palladium in sequential processes. We have elaborated a new catalyzed process with two sequential different steps: allylic alcohol oxidation-Heck reaction. The originality of this system is that the catalyst is involved in both reactions which makes an easy access to functionalized α,β-unsaturated ketones from allylic alcohols.
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Frédéric Batt. Approches synthétiques vers le mycothiazole-4,19-diol : utilisation du palladium en synthèse organique. Autre. Université Claude Bernard - Lyon I, 2009. Français. ⟨NNT : 2009LYO10290⟩. ⟨tel-00654585⟩

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