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Article Dans Une Revue Organic Letters Année : 2021

Bioinspired Early Divergent Oxidative Cyclizations toward Pleiocarpamine, Talbotine, and Strictamine

Résumé

Towards 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 lead 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.

Domaines

Chimie
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Dates et versions

hal-03186900 , version 1 (31-03-2021)

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Citer

Maxime Jarret, Hussein Abou-Hamdan, Cyrille Kouklovsky, Erwan Poupon, Laurent Evanno, et al.. Bioinspired Early Divergent Oxidative Cyclizations toward Pleiocarpamine, Talbotine, and Strictamine. Organic Letters, 2021, 23 (4), pp.1355-1360. ⟨10.1021/acs.orglett.1c00018⟩. ⟨hal-03186900⟩
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