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1. DMSO/Tf2O-mediated cross-coupling of tryptamine with substituted aniline to access C3a-N1'-linked pyrroloindoline alkaloids.

Author

Tayu M, Ishizaki T, Higuchi K, and Kawasaki T

Subjects
Alkaloids chemical synthesis, Stereoisomerism, Alkaloids chemistry, Aniline Compounds chemistry, Dimethyl Sulfoxide chemistry, Indoles chemistry, Mesylates chemistry, Tryptamines chemistry
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.

Published
2015
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