Total Synthesis of (+)-Alstonlarsine A: Old Reactions in Modern Alkaloids Synthesis

Abstract

(+)-Alstonlarsine A is a recently isolated monoterpenoid indole alkaloid, possessing a novel pentacyclic skeleton and interesting biological activity, making it an attractive target for synthetic chemists. In this article we focus on its total synthesis, grounded on enamine formation/Diels–Alder reaction domino sequence, as well as a novel methodology for indole C2 functionalization via carbenoid insertion, which could also allow for the synthesis of other indole alkaloids possessing cycloalka[b]indole subunits.
1 Introduction

2 Diels–Alder Reaction

3 Methodology Studies

4 Total Synthesis of (+)-Alstonlarsine A by Bihelovic and Ferjancic

5 Total Synthesis of (+)-Alstonlarsine A by Zhai

6 Summary

Key words

alkaloid - Diels–Alder - domino reactions - natural products - total synthesis

Publication History

Received: 18 October 2022

Accepted: 26 October 2022

Accepted Manuscript online:
26 October 2022

Article published online:
23 November 2022

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