Synthetic studies on cyathins: Enantioselective total synthesis of (+)-allocyathin B2

Masashi Takano, Akinori Umino, Masahisa Nakada

    Research output: Contribution to journalArticle

    66 Citations (Scopus)

    Abstract

    (Chemical Equation Presented) The enantioselective total synthesis of (+)-allocyathin B2 has been achieved. Our approach features a convergent enantioselective construction of the 5-6-7 tricyclic core system using the originally developed chiral building blocks via asymmetric catalysis, the intramolecular aldol reaction in high yield, successful samarium diiodide-mediated ring expansion, and a newly developed double-bond installation method.

    Original languageEnglish
    Pages (from-to)4897-4900
    Number of pages4
    JournalOrganic Letters
    Volume6
    Issue number26
    DOIs
    Publication statusPublished - 2004 Dec 23

    Fingerprint

    samarium
    Catalysis
    catalysis
    installing
    expansion
    rings
    synthesis
    samarium diiodide
    3-hydroxybutanal
    cyathins
    allocyathin B2

    ASJC Scopus subject areas

    • Molecular Medicine

    Cite this

    Synthetic studies on cyathins : Enantioselective total synthesis of (+)-allocyathin B2. / Takano, Masashi; Umino, Akinori; Nakada, Masahisa.

    In: Organic Letters, Vol. 6, No. 26, 23.12.2004, p. 4897-4900.

    Research output: Contribution to journalArticle

    Takano, Masashi ; Umino, Akinori ; Nakada, Masahisa. / Synthetic studies on cyathins : Enantioselective total synthesis of (+)-allocyathin B2. In: Organic Letters. 2004 ; Vol. 6, No. 26. pp. 4897-4900.
    @article{28c4471155584f2fa88bc430738a9d2c,
    title = "Synthetic studies on cyathins: Enantioselective total synthesis of (+)-allocyathin B2",
    abstract = "(Chemical Equation Presented) The enantioselective total synthesis of (+)-allocyathin B2 has been achieved. Our approach features a convergent enantioselective construction of the 5-6-7 tricyclic core system using the originally developed chiral building blocks via asymmetric catalysis, the intramolecular aldol reaction in high yield, successful samarium diiodide-mediated ring expansion, and a newly developed double-bond installation method.",
    author = "Masashi Takano and Akinori Umino and Masahisa Nakada",
    year = "2004",
    month = "12",
    day = "23",
    doi = "10.1021/ol048010i",
    language = "English",
    volume = "6",
    pages = "4897--4900",
    journal = "Organic Letters",
    issn = "1523-7060",
    publisher = "American Chemical Society",
    number = "26",

    }

    TY - JOUR

    T1 - Synthetic studies on cyathins

    T2 - Enantioselective total synthesis of (+)-allocyathin B2

    AU - Takano, Masashi

    AU - Umino, Akinori

    AU - Nakada, Masahisa

    PY - 2004/12/23

    Y1 - 2004/12/23

    N2 - (Chemical Equation Presented) The enantioselective total synthesis of (+)-allocyathin B2 has been achieved. Our approach features a convergent enantioselective construction of the 5-6-7 tricyclic core system using the originally developed chiral building blocks via asymmetric catalysis, the intramolecular aldol reaction in high yield, successful samarium diiodide-mediated ring expansion, and a newly developed double-bond installation method.

    AB - (Chemical Equation Presented) The enantioselective total synthesis of (+)-allocyathin B2 has been achieved. Our approach features a convergent enantioselective construction of the 5-6-7 tricyclic core system using the originally developed chiral building blocks via asymmetric catalysis, the intramolecular aldol reaction in high yield, successful samarium diiodide-mediated ring expansion, and a newly developed double-bond installation method.

    UR - http://www.scopus.com/inward/record.url?scp=12344338337&partnerID=8YFLogxK

    UR - http://www.scopus.com/inward/citedby.url?scp=12344338337&partnerID=8YFLogxK

    U2 - 10.1021/ol048010i

    DO - 10.1021/ol048010i

    M3 - Article

    C2 - 15606094

    AN - SCOPUS:12344338337

    VL - 6

    SP - 4897

    EP - 4900

    JO - Organic Letters

    JF - Organic Letters

    SN - 1523-7060

    IS - 26

    ER -