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Désaromatisation oxygénante asymétrique de phénols à l'aide d'iodanes pour la synthèse totale de substances naturelles

Abstract : The oxygenative phenol dearomatization reaction is a very useful transformation, as a key step in the synthesis of complex natural substances. It gives access to cyclohexa-2,4-dienones from ortho-substituted phenols, through the use of hypervalent iodine reagents (i.e., iodanes), which constitutes a modern alternative to toxic heavy-metal-based reagents (e.g., Pb, Tl, Hg). Our team is interested in the hydroxylative dearomatization of 2-alkylphenols (HPD reaction) by iodanes, a transformation that results in the formation of one quaternary stereogenic center. Control of the absolute configuration of this chiral center through the use of an appropriate substrate or reagent is amongst our goals. Chiral iodanes recently developed in the laboratory allowed us to reach enantiomeric excesses above 90 % in model HPD reactions. Successful application of these chiral iodanes led us to achieve the first total syntheses of (–)-bacchopetiolone and (+)-maytenone, as well as that of the epoxy ortho- quinol polar head of (+)-scyphostatine.
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Mourad El Assal. Désaromatisation oxygénante asymétrique de phénols à l'aide d'iodanes pour la synthèse totale de substances naturelles. Chimie organique. Université de Bordeaux, 2014. Français. ⟨NNT : 2014BORD0348⟩. ⟨tel-01340868⟩

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