Gold-Catalyzed Atom-Economic Synthesis of Sulfone-Containing Pyrrolo[2,1-<i>a</i>]isoquinolines from Diynamides: Evidence for Consecutive Sulfonyl Migration

Abstract

A gold-catalyzed cascade reaction of conjugated diynamides has been developed. In this way, a series of sulfone-containing pyrrolo[2,1-a]isoquinolines featuring the core structural motifs of lamellarin alkaloids were prepared atom economically. Mechanistic studies including DFT calculations uncovered a consecutive 1,2-migration of the sulfonyl group for the formation of a pyrrole ring.