4.8 Article

Eight-Step Total Synthesis of Phalarine by Bioinspired Oxidative Coupling of Indole and Phenol

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 18, Pages 6074-6078

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201900199

Keywords

alkaloids; natural products; oxidative coupling; regioselectivity; total synthesis

Funding

  1. National Natural Science Foundation of China [21871013, 21572008]

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We report for the first time that the benzofuro[3,2-b]indoline framework could be obtained by PIDA-mediated direct oxidative coupling of 2,3-disubstituted-indoles with phenols. Application of this chemistry allows for an eight-step total synthesis of phalarine from commercially available tryptamine.

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