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Article Dans Une Revue Natural Product Reports Année : 2021

The chemistry of mavacurane alkaloids: a rich source of bis-indole alkaloids

Résumé

This review presents a complete coverage of the mavacuranes alkaloids since the early reports to date. Mavacuranes alkaloids are a restrictive subgroup of monoterpene indole alkaloids (MIA) represented by its two emblematic congeners C-mavacurine and pleiocarpamine. Their skeleton is defined by a bond between the indolic N1 nitrogen and the C16 carbon of the tetracyclic scaffold of the corynanthe group of MIA. A limited number of congeners is known, as this skeleton can be considered as a cul-desac in the main MIA biosynthetic routes. Thanks to an exalted enamine-type reactivity, mavacuranes are frequently involved in the formation of multimeric MIA scaffolds. This review cover isolation aspects and synthetic approaches toward the mavacurane core and bisindoles assemblies. To access the mavacurane core, only few strategies are reported, and the main synthetic difficulties usually originate from the important rigidity of the pentacyclic system. For the bisindoles assemblies, biomimetic routes were privileged and delivered the complex structures using smooth conditions.
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Dates et versions

hal-03186969 , version 1 (31-03-2021)

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Audrey Mauger, Maxime Jarret, Cyrille Kouklovsky, Erwan Poupon, Laurent Evanno, et al.. The chemistry of mavacurane alkaloids: a rich source of bis-indole alkaloids. Natural Product Reports, 2021, 30 (10), pp.1852-1886. ⟨10.1039/D0NP00088D⟩. ⟨hal-03186969⟩
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