Rearrangement of 3-alkyl-1-allylindoles: a model reaction for the biogenesis of echinulin-type compounds

Abstract

The reactivity of 3-alkyl-1-allylindoles as model systems in the biogenesis and synthesis of the echinulin-type compounds has been studied: in the presence of acids the crotyl and γγ-dimethylallyl groups migrate from the 1- to the 2-position of the indole nucleus with a partial allylic rearrangement.