The combination of organolithium chemistry with gold catalysis has enabled the development of a
synthetic strategy for accessing polysubstituted indoles and carbazoles from readily available starting materials.
This method is based on a “back-to-front” approach from ketopyrroles, generated by intramolecular
carbolithiation of N,N-bis-(2-lithioallyl)amines that evolve into 3,4-bis(lithiomethyl)dihydropyrrole intermediates capable of reacting with carboxylic esters and Weinreb amides. These ketopyrroles have demonstrated to
be excellent precursors of mono or bis(alkynols)pyrroles that, under gold-catalysis, experience a
benzannulation reaction providing access to regioselectively substituted indoles or carbazoles.
