Synthesis of the C1-C17 Segment of Bafilomycin N

Haruka Sato, Seijiro Hosokawa

    Research output: Contribution to journalArticle

    Abstract

    The C1-C17 segment of bafilomycin N has been synthesized. The C1-C11 segment was synthesized by the anti -selective vinylogous Mukaiyama aldol reaction with a chiral vinylketene silyl N, O -acetal and the Horner-Wadsworth-Emmons reaction, whereas C12-C17 was constructed by the syn -selective vinylogous Mukaiyama aldol reaction and the Jung's semipinacol rearrangement. Those segments were connected by the Stille coupling to afford the C1-C17 segment.

    Original languageEnglish
    Pages (from-to)577-580
    Number of pages4
    JournalSynlett
    Volume30
    Issue number5
    DOIs
    Publication statusPublished - 2019 Jan 1

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    Acetals
    3-hydroxybutanal
    semipinacol

    Keywords

    • bafilomycin
    • polypropionate
    • semipinacol rearrangement
    • Stille coupling
    • vinylketene silyl N O -acetal
    • vinylogous Mukaiyama aldol reaction

    ASJC Scopus subject areas

    • Organic Chemistry

    Cite this

    Synthesis of the C1-C17 Segment of Bafilomycin N. / Sato, Haruka; Hosokawa, Seijiro.

    In: Synlett, Vol. 30, No. 5, 01.01.2019, p. 577-580.

    Research output: Contribution to journalArticle

    Sato, Haruka ; Hosokawa, Seijiro. / Synthesis of the C1-C17 Segment of Bafilomycin N. In: Synlett. 2019 ; Vol. 30, No. 5. pp. 577-580.
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