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Article Dans Une Revue SYNLETT Année : 2023

Total Synthesis of Mavacuran Alkaloids with Bioinspired and non-Bioinspired Strategies

Résumé

In this account, we report our endeavors towards the total synthesis of the mavacuran alkaloids and some of their highly natural complex bis-indoles. This study started with the hemisynthesis of voacalgine A and bipleiophylline, made an excursion to a related family of monoterpene indole alkaloids (total synthesis of 17-nor-excelsinidine) and ended with the total synthesis of several mavacuran alkaloids (16-epipleiocarpamine, 16-hydroxymethylpleiocarpamine, taberdivarine H, normavacurine, C-mavacurine, C-profluorocurine, and C-fluorocurine) via a combination of bioinspired and non-bioinspired synthetic routes. 1 Introduction 2 Bioinspired hemisynthesis of voacalgine A and bipleiophylline 3 Total synthesis of the mavacuran alkaloids 4 Bioinspired oxidative cyclization of a geissoschizine ammonium derivative to form the N1-C16 bond and E ring 5 Non-bionspired Michael addition to form the C15-C20 bond and the E ring 6 Conclusion
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Dates et versions

hal-04274139 , version 1 (09-11-2023)

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Cyrille Kouklovsky, Erwan Poupon, Laurent Evanno, Guillaume Vincent. Total Synthesis of Mavacuran Alkaloids with Bioinspired and non-Bioinspired Strategies. SYNLETT, 2023, ⟨10.1055/s-0042-1751498⟩. ⟨hal-04274139⟩
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