Studies on the diastereoselectivity in the IMDA reactions of terminally activated (E,E,E)-nona-1,6,8-trienes

Takahiro Suzuki, Natsumi Tanaka, Takehiko Matsumura, Yosuke Hosoya, Masahisa Nakada

    Research output: Contribution to journalArticle

    15 Citations (Scopus)

    Abstract

    The structure-diastereoselectivity relationships in the IMDA reactions of the terminally activated (E,E,E)-nona-1,6,8-trienes have been studied. It is found that the configuration of the C3 position bearing the protected hydroxyl group is crucial to the diastereoselectivity, and the magnitude of the ratio depends on the relative configuration of the C3-C5 positions. The results obtained in this study including the new successful IMDA reactions would be useful for the stereoselective synthesis of natural products containing a bicyclo[4.3.0]non-2-ene carbon skeleton.

    Original languageEnglish
    Pages (from-to)1593-1598
    Number of pages6
    JournalTetrahedron Letters
    Volume47
    Issue number10
    DOIs
    Publication statusPublished - 2006 Mar 6

    Fingerprint

    Bearings (structural)
    Biological Products
    Skeleton
    Hydroxyl Radical
    Carbon

    ASJC Scopus subject areas

    • Biochemistry
    • Organic Chemistry
    • Drug Discovery

    Cite this

    Studies on the diastereoselectivity in the IMDA reactions of terminally activated (E,E,E)-nona-1,6,8-trienes. / Suzuki, Takahiro; Tanaka, Natsumi; Matsumura, Takehiko; Hosoya, Yosuke; Nakada, Masahisa.

    In: Tetrahedron Letters, Vol. 47, No. 10, 06.03.2006, p. 1593-1598.

    Research output: Contribution to journalArticle

    Suzuki, Takahiro ; Tanaka, Natsumi ; Matsumura, Takehiko ; Hosoya, Yosuke ; Nakada, Masahisa. / Studies on the diastereoselectivity in the IMDA reactions of terminally activated (E,E,E)-nona-1,6,8-trienes. In: Tetrahedron Letters. 2006 ; Vol. 47, No. 10. pp. 1593-1598.
    @article{6917af8b2e904c38844c2893cdd77887,
    title = "Studies on the diastereoselectivity in the IMDA reactions of terminally activated (E,E,E)-nona-1,6,8-trienes",
    abstract = "The structure-diastereoselectivity relationships in the IMDA reactions of the terminally activated (E,E,E)-nona-1,6,8-trienes have been studied. It is found that the configuration of the C3 position bearing the protected hydroxyl group is crucial to the diastereoselectivity, and the magnitude of the ratio depends on the relative configuration of the C3-C5 positions. The results obtained in this study including the new successful IMDA reactions would be useful for the stereoselective synthesis of natural products containing a bicyclo[4.3.0]non-2-ene carbon skeleton.",
    author = "Takahiro Suzuki and Natsumi Tanaka and Takehiko Matsumura and Yosuke Hosoya and Masahisa Nakada",
    year = "2006",
    month = "3",
    day = "6",
    doi = "10.1016/j.tetlet.2005.12.118",
    language = "English",
    volume = "47",
    pages = "1593--1598",
    journal = "Tetrahedron Letters",
    issn = "0040-4039",
    publisher = "Elsevier Limited",
    number = "10",

    }

    TY - JOUR

    T1 - Studies on the diastereoselectivity in the IMDA reactions of terminally activated (E,E,E)-nona-1,6,8-trienes

    AU - Suzuki, Takahiro

    AU - Tanaka, Natsumi

    AU - Matsumura, Takehiko

    AU - Hosoya, Yosuke

    AU - Nakada, Masahisa

    PY - 2006/3/6

    Y1 - 2006/3/6

    N2 - The structure-diastereoselectivity relationships in the IMDA reactions of the terminally activated (E,E,E)-nona-1,6,8-trienes have been studied. It is found that the configuration of the C3 position bearing the protected hydroxyl group is crucial to the diastereoselectivity, and the magnitude of the ratio depends on the relative configuration of the C3-C5 positions. The results obtained in this study including the new successful IMDA reactions would be useful for the stereoselective synthesis of natural products containing a bicyclo[4.3.0]non-2-ene carbon skeleton.

    AB - The structure-diastereoselectivity relationships in the IMDA reactions of the terminally activated (E,E,E)-nona-1,6,8-trienes have been studied. It is found that the configuration of the C3 position bearing the protected hydroxyl group is crucial to the diastereoselectivity, and the magnitude of the ratio depends on the relative configuration of the C3-C5 positions. The results obtained in this study including the new successful IMDA reactions would be useful for the stereoselective synthesis of natural products containing a bicyclo[4.3.0]non-2-ene carbon skeleton.

    UR - http://www.scopus.com/inward/record.url?scp=32044445556&partnerID=8YFLogxK

    UR - http://www.scopus.com/inward/citedby.url?scp=32044445556&partnerID=8YFLogxK

    U2 - 10.1016/j.tetlet.2005.12.118

    DO - 10.1016/j.tetlet.2005.12.118

    M3 - Article

    VL - 47

    SP - 1593

    EP - 1598

    JO - Tetrahedron Letters

    JF - Tetrahedron Letters

    SN - 0040-4039

    IS - 10

    ER -