Enantioselective total synthesis of (+)-digitoxigenin

Masahiro Honma, Masahisa Nakada

    Research output: Contribution to journalArticle

    41 Citations (Scopus)

    Abstract

    An enantioselective total synthesis of (+)-digitoxigenin is described. This total synthesis is accomplished in a convergent manner using two chiral fragments prepared via the catalytic asymmetric intramolecular cyclopropanation and baker's yeast mediated reduction developed by us, respectively. This convergent synthesis would be useful for preparing some new derivatives of digitoxigenin for SAR studies and could be applied for the total synthesis of other cardenolides left unprepared.

    Original languageEnglish
    Pages (from-to)1541-1544
    Number of pages4
    JournalTetrahedron Letters
    Volume48
    Issue number9
    DOIs
    Publication statusPublished - 2007 Feb 26

    Fingerprint

    Digitoxigenin
    Cardenolides
    Saccharomyces cerevisiae
    Yeast
    Derivatives

    ASJC Scopus subject areas

    • Biochemistry
    • Organic Chemistry
    • Drug Discovery

    Cite this

    Enantioselective total synthesis of (+)-digitoxigenin. / Honma, Masahiro; Nakada, Masahisa.

    In: Tetrahedron Letters, Vol. 48, No. 9, 26.02.2007, p. 1541-1544.

    Research output: Contribution to journalArticle

    Honma, Masahiro ; Nakada, Masahisa. / Enantioselective total synthesis of (+)-digitoxigenin. In: Tetrahedron Letters. 2007 ; Vol. 48, No. 9. pp. 1541-1544.
    @article{61c587fa0ea1468e9ccc78d9c7a471e4,
    title = "Enantioselective total synthesis of (+)-digitoxigenin",
    abstract = "An enantioselective total synthesis of (+)-digitoxigenin is described. This total synthesis is accomplished in a convergent manner using two chiral fragments prepared via the catalytic asymmetric intramolecular cyclopropanation and baker's yeast mediated reduction developed by us, respectively. This convergent synthesis would be useful for preparing some new derivatives of digitoxigenin for SAR studies and could be applied for the total synthesis of other cardenolides left unprepared.",
    author = "Masahiro Honma and Masahisa Nakada",
    year = "2007",
    month = "2",
    day = "26",
    doi = "10.1016/j.tetlet.2007.01.024",
    language = "English",
    volume = "48",
    pages = "1541--1544",
    journal = "Tetrahedron Letters",
    issn = "0040-4039",
    publisher = "Elsevier Limited",
    number = "9",

    }

    TY - JOUR

    T1 - Enantioselective total synthesis of (+)-digitoxigenin

    AU - Honma, Masahiro

    AU - Nakada, Masahisa

    PY - 2007/2/26

    Y1 - 2007/2/26

    N2 - An enantioselective total synthesis of (+)-digitoxigenin is described. This total synthesis is accomplished in a convergent manner using two chiral fragments prepared via the catalytic asymmetric intramolecular cyclopropanation and baker's yeast mediated reduction developed by us, respectively. This convergent synthesis would be useful for preparing some new derivatives of digitoxigenin for SAR studies and could be applied for the total synthesis of other cardenolides left unprepared.

    AB - An enantioselective total synthesis of (+)-digitoxigenin is described. This total synthesis is accomplished in a convergent manner using two chiral fragments prepared via the catalytic asymmetric intramolecular cyclopropanation and baker's yeast mediated reduction developed by us, respectively. This convergent synthesis would be useful for preparing some new derivatives of digitoxigenin for SAR studies and could be applied for the total synthesis of other cardenolides left unprepared.

    UR - http://www.scopus.com/inward/record.url?scp=33846611583&partnerID=8YFLogxK

    UR - http://www.scopus.com/inward/citedby.url?scp=33846611583&partnerID=8YFLogxK

    U2 - 10.1016/j.tetlet.2007.01.024

    DO - 10.1016/j.tetlet.2007.01.024

    M3 - Article

    VL - 48

    SP - 1541

    EP - 1544

    JO - Tetrahedron Letters

    JF - Tetrahedron Letters

    SN - 0040-4039

    IS - 9

    ER -