Total Synthesis of Diocollettines A via an Acid-Promoted Oxa-Michael-Aldol-Acetalization Cascade

Misaki Kawamoto, Shuntaro Sato, Masaru Enomoto, Yusuke Ogura, Shigefumi Kuwahara

    Research output: Contribution to journalArticlepeer-review

    5 Citations (Scopus)

    Abstract

    A diastereo- and enantioselective total synthesis of diocollettines A with an unusual oxygen-containing tricyclic ring system has been achieved in 63% overall yield from commercially available 3-phenylpropanal via four steps. The key feature of the present synthesis is an exclusively diastereoselective cascade sequence composed of a trans-selective oxa-Michael addition of 1,3-dihydroxyacetone to a 2,3-dihydropyrylium ion intermediate, intramolecular aldol-type reaction, and intramolecular acetalization.

    Original languageEnglish
    Pages (from-to)10099-10101
    Number of pages3
    JournalOrganic letters
    Volume21
    Issue number24
    DOIs
    Publication statusPublished - 2019 Dec 20

    ASJC Scopus subject areas

    • Biochemistry
    • Physical and Theoretical Chemistry
    • Organic Chemistry

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