A general strategy for the synthesis of indoloquinolizine alkaloids: Via a cyanide-catalyzed imino-Stetter reaction

Eunjoon Park, Cheol Hong Cheon

    Research output: Contribution to journalArticlepeer-review

    15 Citations (Scopus)

    Abstract

    A new strategy applicable to the synthesis of indoloquinolizine natural products has been developed. A cyanide-catalyzed intramolecular imino-Stetter reaction of aldimines, derived from 2-aminocinnamic acid derivatives and 2-pyridinecarboxaldehydes, provided indole-3-acetic acid derivatives bearing a pyridyl ring at the 2-position. Reduction of the carboxylic acid moiety to an alcohol followed by activation of the resulting alcohol with Tf2O or TsCl generated indoloquinolizinium salts, which were utilized as precursors for indoloquinolizine natural products. The advantage of this protocol was successfully demonstrated in the total syntheses of arborescidine A and nauclefidine.

    Original languageEnglish
    Pages (from-to)10265-10275
    Number of pages11
    JournalOrganic and Biomolecular Chemistry
    Volume15
    Issue number48
    DOIs
    Publication statusPublished - 2017

    Bibliographical note

    Publisher Copyright:
    © 2017 The Royal Society of Chemistry.

    ASJC Scopus subject areas

    • Biochemistry
    • Physical and Theoretical Chemistry
    • Organic Chemistry

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