Asymmetric Total Synthesis of Iheyamine B

Jiye Jeon, Cheol Hong Cheon

    Research output: Contribution to journalArticlepeer-review

    12 Citations (Scopus)

    Abstract

    Herein, we report the first asymmetric total synthesis of iheyamine B from 2,2′-bisindoloazepinone using the stereoselective construction of the trans-vicinal 2-oxopropyl moiety in the azepine scaffold. The asymmetric decarboxylative allylic alkylation provided the α-allylated 2,2′-bisindoloazepinone intermediate. The subsequent conversion of the lactam moiety into another allyl group in a trans-selective manner followed by Wacker oxidation of each allyl unit to the corresponding 2-oxopropyl group completed the total synthesis of iheyamine B.

    Original languageEnglish
    Pages (from-to)7128-7133
    Number of pages6
    JournalOrganic Letters
    Volume24
    Issue number39
    DOIs
    Publication statusPublished - 2022 Oct 7

    Bibliographical note

    Funding Information:
    This study was supported by the National Research Foundation of Korea (NRF) grants funded by the Korean Government {NRF-2021R1A2C1012984 and NRF-2021R1A5A6002803, (Center for New Directions in Organic Synthesis)}. J.J. acknowledges the financial support from the NRF-2018 Fostering Core Leaders of the Future Basic Science Program/Global Ph.D. Fellowship Program funded by the Korean Government. We dedicated this work to Professor Jung-Il Jin on the occasion of his 80th birthday.

    Publisher Copyright:
    © 2022 American Chemical Society. All rights reserved.

    ASJC Scopus subject areas

    • Biochemistry
    • Physical and Theoretical Chemistry
    • Organic Chemistry

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