Enantioselective total synthesis of (+)-ophiobolin A

Kazuhiro Tsuna, Naoyoshi Noguchi, Masahisa Nakada

    Research output: Contribution to journal › Article

    25 Citations (Scopus)

    Abstract

    The enantioselective total synthesis of (+)-ophiobolin A is described. This total synthesis features the construction of the spiro CD ring of (+)-ophiobolin A through a stereoselective intramolecular Hosomi-Sakurai cyclization reaction, the joining of the A ring to the CD ring by using a reaction reported by Utimoto, and the construction of the ophiobolin eight-membered carbocyclic ring through ring-closing metathesis (RCM), which was performed for the first time in this study. This successful RCM reaction required the use of a substrate that contained either a benzyloxy or a methoxymethoxy group at the C5 position and either an isopropenyl group or its hydroxylated form at the C6 position.

    Original languageEnglish
    Pages (from-to)5476-5486
    Number of pages11
    JournalChemistry - A European Journal
    Volume19
    Issue number17
    DOIs
    Publication statusPublished - 2013 Apr 22

    Fingerprint

    Cyclization
    Joining
    Substrates
    ophiobolin A
    ophiobolins

    Keywords

    • cyclization
    • natural products
    • ophiobolin A
    • spiro compounds
    • total synthesis

    ASJC Scopus subject areas

    • Chemistry(all)

    Cite this

    Enantioselective total synthesis of (+)-ophiobolin A. / Tsuna, Kazuhiro; Noguchi, Naoyoshi; Nakada, Masahisa.

    In: Chemistry - A European Journal, Vol. 19, No. 17, 22.04.2013, p. 5476-5486.

    Research output: Contribution to journal › Article

    Tsuna, K, Noguchi, N & Nakada, M 2013, 'Enantioselective total synthesis of (+)-ophiobolin A', Chemistry - A European Journal, vol. 19, no. 17, pp. 5476-5486. https://doi.org/10.1002/chem.201204119
    Tsuna K, Noguchi N, Nakada M. Enantioselective total synthesis of (+)-ophiobolin A. Chemistry - A European Journal. 2013 Apr 22;19(17):5476-5486. https://doi.org/10.1002/chem.201204119
    Tsuna, Kazuhiro ; Noguchi, Naoyoshi ; Nakada, Masahisa. / Enantioselective total synthesis of (+)-ophiobolin A. In: Chemistry - A European Journal. 2013 ; Vol. 19, No. 17. pp. 5476-5486.
    @article{b88ed008acad4ed0abf7c368be93278a,
    title = "Enantioselective total synthesis of (+)-ophiobolin A",
    abstract = "The enantioselective total synthesis of (+)-ophiobolin A is described. This total synthesis features the construction of the spiro CD ring of (+)-ophiobolin A through a stereoselective intramolecular Hosomi-Sakurai cyclization reaction, the joining of the A ring to the CD ring by using a reaction reported by Utimoto, and the construction of the ophiobolin eight-membered carbocyclic ring through ring-closing metathesis (RCM), which was performed for the first time in this study. This successful RCM reaction required the use of a substrate that contained either a benzyloxy or a methoxymethoxy group at the C5 position and either an isopropenyl group or its hydroxylated form at the C6 position.",
    keywords = "cyclization, natural products, ophiobolin A, spiro compounds, total synthesis",
    author = "Kazuhiro Tsuna and Naoyoshi Noguchi and Masahisa Nakada",
    year = "2013",
    month = "4",
    day = "22",
    doi = "10.1002/chem.201204119",
    language = "English",
    volume = "19",
    pages = "5476--5486",
    journal = "Chemistry - A European Journal",
    issn = "0947-6539",
    publisher = "Wiley-VCH Verlag",
    number = "17",

    }

    TY - JOUR

    T1 - Enantioselective total synthesis of (+)-ophiobolin A

    AU - Tsuna, Kazuhiro

    AU - Noguchi, Naoyoshi

    AU - Nakada, Masahisa

    PY - 2013/4/22

    Y1 - 2013/4/22

    N2 - The enantioselective total synthesis of (+)-ophiobolin A is described. This total synthesis features the construction of the spiro CD ring of (+)-ophiobolin A through a stereoselective intramolecular Hosomi-Sakurai cyclization reaction, the joining of the A ring to the CD ring by using a reaction reported by Utimoto, and the construction of the ophiobolin eight-membered carbocyclic ring through ring-closing metathesis (RCM), which was performed for the first time in this study. This successful RCM reaction required the use of a substrate that contained either a benzyloxy or a methoxymethoxy group at the C5 position and either an isopropenyl group or its hydroxylated form at the C6 position.

    AB - The enantioselective total synthesis of (+)-ophiobolin A is described. This total synthesis features the construction of the spiro CD ring of (+)-ophiobolin A through a stereoselective intramolecular Hosomi-Sakurai cyclization reaction, the joining of the A ring to the CD ring by using a reaction reported by Utimoto, and the construction of the ophiobolin eight-membered carbocyclic ring through ring-closing metathesis (RCM), which was performed for the first time in this study. This successful RCM reaction required the use of a substrate that contained either a benzyloxy or a methoxymethoxy group at the C5 position and either an isopropenyl group or its hydroxylated form at the C6 position.

    KW - cyclization

    KW - natural products

    KW - ophiobolin A

    KW - spiro compounds

    KW - total synthesis

    UR - http://www.scopus.com/inward/record.url?scp=84876217697&partnerID=8YFLogxK

    UR - http://www.scopus.com/inward/citedby.url?scp=84876217697&partnerID=8YFLogxK

    U2 - 10.1002/chem.201204119

    DO - 10.1002/chem.201204119

    M3 - Article

    VL - 19

    SP - 5476

    EP - 5486

    JO - Chemistry - A European Journal

    JF - Chemistry - A European Journal

    SN - 0947-6539

    IS - 17

    ER -

    Access to Document