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
Origine : Fichiers produits par l'(les) auteur(s)