The chemistry of mavacurane alkaloids: a rich source of bis-indole alkaloids
- 5 March 2021
- journal article
- review article
- Published by Royal Society of Chemistry (RSC) in Natural Product Reports
- Vol. 38 (10), 1852-1886
- https://doi.org/10.1039/d0np00088d
Abstract
Covering: since early reports up to the end of 2020 This review presents a complete coverage of the mavacuranes alkaloids since early reports till date. Mavacuranes alkaloids are a restrictive sub-group of monoterpene indole alkaloids (MIAs), which are represented by their two emblematic congeners, namely, 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 in MIA. A limited number of congeners is known as this skeleton can be considered as a cul-de-sac in main MIA biosynthetic routes. Thanks to the enhanced enamine-type reactivity, mavacuranes are frequently involved in the formation of multimeric MIA scaffolds. This review covers isolation aspects and synthetic approaches towards the mavacurane core and bisindole assemblies. To access the mavacurane core, only a few strategies are reported and the main synthetic difficulties usually originate from the important rigidity of the pentacyclic system. For the bisindole assemblies, biomimetic routes are privileged and deliver complex structures using smooth conditions.Keywords
Funding Information
- Ministère de l'Enseignement Supérieur et de la Recherche (PhD fellowship to Audrey Mauger)
- Agence Nationale de la Recherche (ANR-15-CE29-0001 (“Mount Indole”))
- Centre National de la Recherche Scientifique
- Université Paris-Saclay
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