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Contribution à la synthèse totale de l'alcaloïde (-)-205B

Abstract : A non-chiral pool approach to the 8b-azaacenaphthylene ring system of the frog poison alkaloid (-)-205B has been developed. This rare tricyclic alkaloid has been of considerable synthetic interest in recent years owing to its potential biological activity against neuronal disorders. However, due to lack of material, a detailed study of the mode of action of this natural product has not yet been reported. Our strategy features several noteworthy transformations. A highly diastereoselective thermal [2+2] cycloaddition and a ring expansion through Beckmann rearrangement generates the functionalised lactam intermediate. An efficient vinylogous Mannich reaction then provides access to a butenolide, which subsequently leads to an indolizidinone ring system. After installation of a methyl group on this bicyclic intermediate, a relatively unexplored aza-Prins cyclization has been successfully employed to obtain an advanced intermediate, possessing the desired tricyclic system found in the natural product. This approach has laid a solid foundation for a novel access to this potentially important but scarce alkaloid extracted from a neotropical frog Dendrobatus pumilio that is threatened to be endangered.
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Submitted on : Wednesday, July 20, 2011 - 11:13:24 AM
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Anushree Kamath. Contribution à la synthèse totale de l'alcaloïde (-)-205B. Chimie organique. Université de Grenoble, 2011. Français. ⟨NNT : 2011GRENV021⟩. ⟨tel-00609829⟩

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