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Approche synthétique du fragment C28-C46 de l'Hémicalide. Synthèse de delta-lactones fonctionnalisées.

Abstract : The work described in this manuscript concerns the synthesis of the C28-C46 fragment of Hemicalide, a natural product extracted from a marine sponge exhibiting a highly potent antitumoral activity. The key steps of the synthesis are : a diastereoselective conjugate addition of a vinyl boroante on an unsaturated lactone, hydrogenation and hydrogenation to control the centers C39, C40 and C42, respectively. The C34-C35 double bond was created by a Julia-Kocienski olefination. During this work, a new method for the diastereoselective synthesis of delta-lactones was developed, involving a sigmatropic rearrangement and a cyclization catalyzed by transition metal complexes.
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https://tel.archives-ouvertes.fr/tel-01940063
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  • HAL Id : tel-01940063, version 1

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Guillaume Boissonnat. Approche synthétique du fragment C28-C46 de l'Hémicalide. Synthèse de delta-lactones fonctionnalisées.. Chimie organique. Université Pierre et Marie Curie - Paris VI, 2016. Français. ⟨NNT : 2016PA066641⟩. ⟨tel-01940063⟩

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