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Vers la synthèse totale de l'amphidinol 3 : contrôle de la stéréoséquence C20-C27

Abstract : Amphidinols are a new class of polyketide extracted from dinoflagellates and exhib promising biological activities, such as antifungal and hemolytic. The amphidinol-3 is the only amphidinol possessing its fully elucidated structure and is the most biologically potent.The C17-C30 fragment is the first goal of our research. The synthesis is based on sulfoxide as chiral auxiliary and on a bromoallylsilane as bifunctionnal central core. All stereogenic centers are fully controlled with high diastereomeric ratios except the one bearing a methyl in C23 position. The lack of selectivity during the hydrogenation affording the C23 stereogenic center and plausible failures of fragment couplings force us to explore a new retrosynthesis. Our second goal is the synthesis of C13-C29 fragment. The new strategy is based on a coupling between a 1,3-dithiane derivative and an α-branched aldehyde. After protecting group optimization, the C13-C29 fragment is synthetized with all its stereogenic centers fully controlled.
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Nicolas Rival. Vers la synthèse totale de l'amphidinol 3 : contrôle de la stéréoséquence C20-C27. Autre. Université de Strasbourg, 2012. Français. ⟨NNT : 2012STRAF056⟩. ⟨tel-00832516⟩

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