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Approches synthétiques aux fragments spiroimines du 13-desméthyle spirolide C et de la gymnodimine

Abstract : The Gymnodimine and the 13-desméthyle Spirolide C are two macrocyclic neurotoxins bearing a cyclic imine. They were isolated in filter organisms such as mussel and oysters and are produced by marine unicellular organisms called dinoflagellates. In the occurrence of algal blooms, a massive production of these molecules creates public health issues. The absorption and concentration by filter organisms, allow this molecules to be delivered to marine wild life and human trough the food chain. To date, the mode of action of spirolides is not fully elucidated and the toxicity toward humans still needs studies. Considering their low bioavailability, their synthesis proves to be crucial to have enough material for pharmacological studies. This manuscript present the synthesis of the spiroimine fragment of the 13-desméthyle Spirolide C and the Gymnodimine. Various unified strategies were tested in this work. In the first part, cationic and radical cyclisations of epoxy-allylsilanes obtained by a key allylic substitution are presented. In the second part, a diastereoselective approach for the synthesis of allylsilanes and cyclisation attempts by radical opening of epoxides are presented. Finally, a Diels-Alder based strategy allowed the synthesis of a model cyclic imine and a highly substituted fragment for the total synthesis of the Gymnodimine.
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Alexandre Guthertz. Approches synthétiques aux fragments spiroimines du 13-desméthyle spirolide C et de la gymnodimine. Chimie organique. Université de Bordeaux, 2015. Français. ⟨NNT : 2015BORD0342⟩. ⟨tel-01711273⟩

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