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

Key words

monoterpene indole alkaloids - bipleiophylline - pleiocarpamine - C-mavacurine - taberdivarine H - C-fluorocurine - biomimetic - oxidative coupling

Publication History

Received: 14 July 2023

Accepted after revision: 23 August 2023

Article published online:
02 November 2023

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