Through careful choice of conditions, 2-(N-indolyl) amides can be directed to undergo selectively either enolate arylation to give oxindoles or direct arylation to give indolo-fused benzodiazepines. The former chemistry facilitates the synthesis of the hexahydropyrrolindole core of psychotrimine.
Watson, E. L., Ball, A., Raw, S. A., & Marsden, S. P. (2016). Synthetic Studies on Psychotrimine: Palladium-Catalysed Arylation of 2-(N -Indolyl) Amides. Synlett, 27(1), 146-150. https://doi.org/10.1055/s-0035-1560519