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Synthesis of a poison frog bioactive alkaloids

Abstract : Alkaloids are widely occurring compounds in nature. The increasing scope of pharmacological properties displayed by the alkaloids extracted from a neotropical frog Dendrobates pumilio has arouse an intense interest in their study, both from a synthetic and biological aspect. The interest toward the alkaloid (-)-205B has not been considered in our laboratory solely because of the challenged 8b-azaacenaphthylene ring structure, but also was inspired by the promising biological activity it might possess against neuronal disorders.An efficient and highly stereoselective synthetic strategy was developed for the synthesis of the alkaloid (-)-205B. This approach features three characteristic transformations for building up the tricyclic core and installing the main stereochemistry: a 2+2 cycloaddition, a vinylogous Mannich reaction and an aza-Prins cyclization. In tandem with this total synthesis, a novel methodology was developed focusing on the stereo-directed alkylation based on silicon-tethered chemistry that comes up as an efficient solution for a difficulty encountered within the earlier approach.
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Sara Mazeh. Synthesis of a poison frog bioactive alkaloids. Organic chemistry. Université Grenoble Alpes, 2019. English. ⟨NNT : 2019GREAV043⟩. ⟨tel-02613846⟩

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