Etudes vers la synthèse totale de la (-)-lémonomycine. Synthèse d'acides beta-aminés fonctionnalisés par ouverture nucléophile d'aziridiniums dérivés de la sérine.

Abstract : The scientific project was to develop a study for the synthesis of lémonomycine. The lémonomycine is part of a large class of natural products, the tetrahydroisoquinolines which are potent cytotoxic agents and possess many biological activities as antitumor agents and antibiotics. The lémonomycine consists of four cycles, the left and up the tetrahydroisoquinoline part straight ground-diaza-bicyclo [3.2.1]-octane. Moreover, despite the large number of products isolated and synthetic analogs, the presence of a derivative is unique in this sweet family and makes the total synthesis of lémonomycine extremely attractive. Various strategies have been developed to allow the construction of the ground tetracyclic or reason diaza-bicyclo-[3,2,1] octane. This study is based on different milestones such as Pictet-Spengler reaction and Mannich-type cyclizations. These strategies involve cyclizations using different nucleophiles on N-type intermediate acyliminium. Coupled with his synthetic study, we described a method synthesize a wide variety of β-diamino esters and α, β-diamino esters from the serine and regioselectively enantiopure. The simplicity of this procedure and the absence racemization or β-elimination products are obtained by a method of choice for the synthesis of amino acid non-protein.
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Cédric Couturier. Etudes vers la synthèse totale de la (-)-lémonomycine. Synthèse d'acides beta-aminés fonctionnalisés par ouverture nucléophile d'aziridiniums dérivés de la sérine.. Génie chimique. Ecole Polytechnique X, 2005. Français. ⟨pastel-00001605⟩

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