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Scalable total syntheses of N-linked tryptamine dimers by direct indole-aniline coupling: Psychotrimine and kapakahines B and F

Academic Article
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Overview

related to degree

  • Newhouse, Timothy, Ph.D. in Chemistry, Scripps Research 2006 - 2010

authors

  • Newhouse, Timothy
  • Lewis, C. A.
  • Eastman, K. J.
  • Baran, Phil

publication date

  • May 2010

journal

  • Journal of the American Chemical Society  Journal

abstract

  • 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.

subject areas

  • Aniline Compounds
  • Cell Line, Tumor
  • Dimerization
  • Humans
  • Indole Alkaloids
  • Indoles
  • Inhibitory Concentration 50
  • Nitrogen
  • Oxidation-Reduction
  • Peptides, Cyclic
  • Stereoisomerism
  • Substrate Specificity
  • Tryptamines
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Identity

PubMed Central ID

  • PMC2874090

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja1009458

PubMed ID

  • 20426477
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Additional Document Info

start page

  • 7119

end page

  • 7137

volume

  • 132

issue

  • 20

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