1222097-98-4Relevant academic research and scientific papers
Total synthesis of kapakahine e and F
Espejo, Vinson R.,Rainier, Jon D.
supporting information; experimental part, p. 2154 - 2157 (2010/08/05)
Figure presented The total synthesis of the cyclic peptides kapakahine E and F using bromopyrroloindoline heterodimerization reactions, indoline to α-carboline rearrangements, and Negishi coupling reactions is described.
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; scheme or table, 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.
