Synthesis of the C1-C17 Segment of Bafilomycin N

Haruka Sato, Seijiro Hosokawa

    研究成果: Article

    抄録

    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.

    元の言語English
    ページ(範囲)577-580
    ページ数4
    ジャーナルSynlett
    30
    発行部数5
    DOI
    出版物ステータスPublished - 2019 1 1

    Fingerprint

    Acetals
    3-hydroxybutanal
    semipinacol

    ASJC Scopus subject areas

    • Organic Chemistry

    これを引用

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

    :: Synlett, 巻 30, 番号 5, 01.01.2019, p. 577-580.

    研究成果: Article

    Sato, Haruka ; Hosokawa, Seijiro. / Synthesis of the C1-C17 Segment of Bafilomycin N. :: Synlett. 2019 ; 巻 30, 番号 5. pp. 577-580.
    @article{ff094a6a153a459ca446f026e3e0b227,
    title = "Synthesis of the C1-C17 Segment of Bafilomycin N",
    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.",
    keywords = "bafilomycin, polypropionate, semipinacol rearrangement, Stille coupling, vinylketene silyl N O -acetal, vinylogous Mukaiyama aldol reaction",
    author = "Haruka Sato and Seijiro Hosokawa",
    year = "2019",
    month = "1",
    day = "1",
    doi = "10.1055/s-0037-1611727",
    language = "English",
    volume = "30",
    pages = "577--580",
    journal = "Synlett",
    issn = "0936-5214",
    publisher = "Georg Thieme Verlag",
    number = "5",

    }

    TY - JOUR

    T1 - Synthesis of the C1-C17 Segment of Bafilomycin N

    AU - Sato, Haruka

    AU - Hosokawa, Seijiro

    PY - 2019/1/1

    Y1 - 2019/1/1

    N2 - 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.

    AB - 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.

    KW - bafilomycin

    KW - polypropionate

    KW - semipinacol rearrangement

    KW - Stille coupling

    KW - vinylketene silyl N O -acetal

    KW - vinylogous Mukaiyama aldol reaction

    UR - http://www.scopus.com/inward/record.url?scp=85062366671&partnerID=8YFLogxK

    UR - http://www.scopus.com/inward/citedby.url?scp=85062366671&partnerID=8YFLogxK

    U2 - 10.1055/s-0037-1611727

    DO - 10.1055/s-0037-1611727

    M3 - Article

    VL - 30

    SP - 577

    EP - 580

    JO - Synlett

    JF - Synlett

    SN - 0936-5214

    IS - 5

    ER -