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

(+)-Alstonlarsine A is a recently isolated monoterpenoid in dole 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