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Vers la synthèse totale du 13-desméthyle spirolide C. Synthèse d’hétérocycles par activation C–H catalysée au Rh(III)

Abstract : Some marine shellfish toxins in the spiroimine family like gymnodimine and spirolides are produced by dinoflagellates and can be transferred and concentrated in seafood then by vectorial transport they can reach marine animals and humans. Biological studies have shown that these toxins are potent antagonists of the nicotinic acetylcholine receptors (nAChRs) and have a moderate selectivity for subtypes receptor. In the laboratory, we are interested in the total synthesis of gymnodimine and 13-desmethyl spirolide C in order to produce a larger quantity of these molecules (compared to isolation from dinoflagellates) to further investigate their biological activities. In this regard, we developed two complementary approaches to access the spiroimine pattern of these molecules. The first one is based on a decarboxylative asymmetric allylic alkylation reaction. The second uses an intermolecular Diels-Alder reaction.With the need of more sophisticated scaffolds for medicinal chemistry or total synthesis, the development of appropriate ortho-directed C_H activation reactions have proven recently to be crucial. Herein, we propose two simple and efficient intramolecular cyclisation reactions, involving a methoxy-amide directing group and a Rh(III)-catalysis. Synthesis of spiropiperidines and azepinones are presented.
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Augustin Peneau. Vers la synthèse totale du 13-desméthyle spirolide C. Synthèse d’hétérocycles par activation C–H catalysée au Rh(III). Chimie organique. Université Paris-Saclay, 2018. Français. ⟨NNT : 2018SACLS410⟩. ⟨tel-02132282⟩

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