(+)-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. © 2023 Georg Thieme Verlag. All rights reserved.