Total Synthesis of Iheyamine A via the Cyanide-Catalyzed Imino-Stetter Reaction

Jiye Jeon, Hyung Joo Kim, Cheol Hong Cheon

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    19 Citations (Scopus)

    Abstract

    The total synthesis of iheyamine A from readily available ethyl 2-aminocinnamate and 5-methoxyindole-2-carboxaldehyde is described. The cyanide-catalyzed imino-Stetter reaction of an aldimine derived from ethyl 2-aminocinnamate and 5-methoxyindole-2-carboxaldehyde provided the desired unsymmetrical 2,2′-bisindole-3-acetic acid derivative. The subsequent introduction of an amino group at the C-3′ position, followed by the formation of the azepine ring, completed the total synthesis of iheyamine A.

    Original languageEnglish
    Pages (from-to)8149-8156
    Number of pages8
    JournalJournal of Organic Chemistry
    Volume85
    Issue number12
    DOIs
    Publication statusPublished - 2020 Jun 19

    Bibliographical note

    Publisher Copyright:
    Copyright © 2020 American Chemical Society.

    ASJC Scopus subject areas

    • Organic Chemistry

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