1227608-27-6Relevant articles and documents
Scalable total syntheses of N -linked tryptamine dimers by direct indole-aniline coupling: Psychotrimine and kapakahines B and F
Newhouse, Timothy,Lewis, Chad A.,Eastman, Kyle J.,Baran, Phil S.
supporting information; experimental part, p. 7119 - 7137 (2010/07/09)
This report details the invention of a method to enable syntheses of psychotrimine (1) and the kapakahines F and B (2, 3) on a gram scale and in a minimum number of steps. Mechanistic inquiries are presented for the key enabling quaternization of indole at the C3 position by electrophilic attack of an activated aniline species. Excellent chemo-, regio-, and diastereoselectivities are observed for reactions with o-iodoaniline, an indole cation equivalent. Additionally, the scope of this reaction is broad with respect to the tryptamine and aniline components. The anti-cancer profiles of 1-3 have also been evaluated.