Total Synthesis of Luotonin A and Rutaecarpine from an Aldimine via the Designed Cyclization

Se Hyun Kwon, Hong Ahn Seo, Cheol Hong Cheon

    Research output: Contribution to journalArticlepeer-review

    69 Citations (Scopus)

    Abstract

    The total synthesis of rutaecarpine (1) and luotonin A (2) is described through controlled cyclization of a common aldimine intermediate 5 derived from ethyl-2-aminocinnamate and quinazolinone-2-carbaldehyde. The cyanide-mediated imino-Stetter reaction of aldimine 5 provided the corresponding indole derivative 3, from which the total synthesis of rutaecarpine (1) was completed via the formation of a 6-membered C-ring. On the other hand, microwave-assisted thermal 6π-electrocyclization of the common intermediate 5, followed by the formation of a 5-membered C′-ring, allowed the completion of the total synthesis of luotonin A (2).

    Original languageEnglish
    Pages (from-to)5280-5283
    Number of pages4
    JournalOrganic Letters
    Volume18
    Issue number20
    DOIs
    Publication statusPublished - 2016 Oct 21

    Bibliographical note

    Funding Information:
    This work was supported by National Research Foundation of Korea (NRF) grants funded by the Korean Government (NRF- 2015R1D1A1A01057200 and NRF-20100020209). C.-H.C. is also thankful for financial support from an NRF grant funded by the Korean Government (NRF-2014-011165; Center for New Directions in Organic Synthesis).

    Publisher Copyright:
    © 2016 American Chemical Society.

    Copyright:
    Copyright 2016 Elsevier B.V., All rights reserved.

    ASJC Scopus subject areas

    • Biochemistry
    • Physical and Theoretical Chemistry
    • Organic Chemistry

    Fingerprint

    Dive into the research topics of 'Total Synthesis of Luotonin A and Rutaecarpine from an Aldimine via the Designed Cyclization'. Together they form a unique fingerprint.

    Cite this