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

Author:

Tayu Masanori123,Ishizaki Takako123,Higuchi Kazuhiro123,Kawasaki Tomomi123

Affiliation:

1. Meiji Pharmaceutical University

2. Kiyose

3. Japan

Abstract

The cross-coupling of tryptamine with substituted aniline to C3a–nitrogen-linked pyrroloindolines has been developedviathe consecutive cyclization of tryptamine with DMSO/Tf2O and the substitution of 3a-pyrroloindolylthionium intermediate with aniline.

Funder

Japan Society for the Promotion of Science

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Reference33 articles.

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2. T. Hino and M.Nakagawa, in The Alkaloids: Chemistry and Pharmacology, ed. A. Brossi, Academic Press, San Diego, 1988, vol. 34, ch. 1, p. 1

3. U. Anthoni , C.Christophersen and P. H.Nielsen, in Alkaloids: Chemical and Biological Perspectives, ed. S. W. Pelletier, Pergamon, Amsterdam, 1999, vol. 13, ch. 2, p. 163

4. T.-S. Kam and Y.-M.Choo, in The Alkaloids: Chemistry and Biology, ed. G. A. Cordell, Academic Press, 2006, vol. 63, ch. 4, p. 181

5. Total Synthesis of Complex Cyclotryptamine Alkaloids: Stereocontrolled Construction of Quaternary Carbon Stereocenters

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