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Title: Bioinspired Early Divergent Oxidative Cyclizations toward Pleiocarpamine, Talbotine, and Strictamine. Author: Jarret M, Abou-Hamdan H, Kouklovsky C, Poupon E, Evanno L, Vincent G. Journal: Org Lett; 2021 Feb 19; 23(4):1355-1360. PubMed ID: 33522824. Abstract: Toward the mavacurane and akuammilane monoterpene indole alkaloids, we developed divergent oxidative couplings between the indole nucleus (at N1 or C7) and the C16-malonate of a common tricyclic model related to strictosidine according to a biosynthetic hypothesis postulated by Hesse and Schmid. These oxidative cyclizations led selectively to the formation of the N1-C16 bond of pleiocarpamine or to the C7-C16 bond of strictamine. We were then able to obtain the scaffold of talbotine.[Abstract] [Full Text] [Related] [New Search]