Total Synthesis of Mavacuran Alkaloids via Bioinspired and Non-Bioinspired Strategies

Abstract In this account, we report our endeavors towards the total synthesis of the mavacuran alkaloids and some of their highly natural complex bis-indoles. Our studies 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 syntheses of several mavacuran alkaloids (16-epi-pleiocarpamine, 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 the E Ring 5 Non-Bioinspired Michael Addition to Form the C15–C20 Bond and the E Ring 6 Conclusion 7 Epilogue