Jump to main content
Jump to site search

Issue 13, 2015
Previous Article Next Article

DMSO/Tf2O-mediated cross-coupling of tryptamine with substituted aniline to access C3a–N1′-linked pyrroloindoline alkaloids

Author affiliations

Abstract

The cross-coupling of tryptamine with substituted aniline to access C3a–nitrogen-linked pyrroloindolines has been developed via the consecutive cyclization of tryptamine with DMSO/Tf2O and the substitution of 3a-pyrroloindolylthionium intermediate with aniline. The use of 2,3-dihydrotryptamine instead of aniline enabled easy access to 3a-(1-indolyl)pyrroloindoline and the concise synthesis of C3a–N1′-linked pyrroloindoline alkaloid (±)-psychotriasine was accomplished.

Graphical abstract: DMSO/Tf2O-mediated cross-coupling of tryptamine with substituted aniline to access C3a–N1′-linked pyrroloindoline alkaloids

Back to tab navigation

Supplementary files

Publication details

The article was received on 30 Jan 2015, accepted on 18 Feb 2015 and first published on 18 Feb 2015


Article type: Communication
DOI: 10.1039/C5OB00190K
Author version available: Download Author version (PDF)
Citation: Org. Biomol. Chem., 2015,13, 3863-3865
  •   Request permissions

    DMSO/Tf2O-mediated cross-coupling of tryptamine with substituted aniline to access C3a–N1′-linked pyrroloindoline alkaloids

    M. Tayu, T. Ishizaki, K. Higuchi and T. Kawasaki, Org. Biomol. Chem., 2015, 13, 3863
    DOI: 10.1039/C5OB00190K

Search articles by author

Spotlight

Advertisements