Synthetic studies on the bioactive tetramic acid JBIR-22 using a late stage Diels-Alder reaction

Alan Healy, N. J. Westwood

    Research output: Contribution to journalArticle

    Abstract

    A late stage Diels-Alder reaction is used to prepare a mixture of JBIR-22, a natural product from the Equisetin family of tetramic acids, and one of its diastereomers. This is achieved in just 8 steps from pyruvate. The success of the late stage DA approach is discussed in the context of the biosynthesis of JBIR-22 (and perhaps related natural products).

    Original languageEnglish (US)
    Pages (from-to)10527-10531
    Number of pages5
    JournalOrganic and Biomolecular Chemistry
    Volume13
    Issue number42
    DOIs
    StatePublished - Jan 1 2015

    Fingerprint

    Diels-Alder reactions
    Cycloaddition Reaction
    activity (biology)
    Biological Products
    pyruvates
    acids
    biosynthesis
    Biosynthesis
    products
    Pyruvic Acid
    tetramic acid
    JBIR-22
    equisetin

    ASJC Scopus subject areas

    • Biochemistry
    • Physical and Theoretical Chemistry
    • Organic Chemistry

    Cite this

    Synthetic studies on the bioactive tetramic acid JBIR-22 using a late stage Diels-Alder reaction. / Healy, Alan; Westwood, N. J.

    In: Organic and Biomolecular Chemistry, Vol. 13, No. 42, 01.01.2015, p. 10527-10531.

    Research output: Contribution to journalArticle

    @article{6b7438fdd1af4829a1dbb7c45fcaf282,
    title = "Synthetic studies on the bioactive tetramic acid JBIR-22 using a late stage Diels-Alder reaction",
    abstract = "A late stage Diels-Alder reaction is used to prepare a mixture of JBIR-22, a natural product from the Equisetin family of tetramic acids, and one of its diastereomers. This is achieved in just 8 steps from pyruvate. The success of the late stage DA approach is discussed in the context of the biosynthesis of JBIR-22 (and perhaps related natural products).",
    author = "Alan Healy and Westwood, {N. J.}",
    year = "2015",
    month = "1",
    day = "1",
    doi = "10.1039/c5ob01771h",
    language = "English (US)",
    volume = "13",
    pages = "10527--10531",
    journal = "Organic and Biomolecular Chemistry",
    issn = "1477-0520",
    publisher = "Royal Society of Chemistry",
    number = "42",

    }

    TY - JOUR

    T1 - Synthetic studies on the bioactive tetramic acid JBIR-22 using a late stage Diels-Alder reaction

    AU - Healy, Alan

    AU - Westwood, N. J.

    PY - 2015/1/1

    Y1 - 2015/1/1

    N2 - A late stage Diels-Alder reaction is used to prepare a mixture of JBIR-22, a natural product from the Equisetin family of tetramic acids, and one of its diastereomers. This is achieved in just 8 steps from pyruvate. The success of the late stage DA approach is discussed in the context of the biosynthesis of JBIR-22 (and perhaps related natural products).

    AB - A late stage Diels-Alder reaction is used to prepare a mixture of JBIR-22, a natural product from the Equisetin family of tetramic acids, and one of its diastereomers. This is achieved in just 8 steps from pyruvate. The success of the late stage DA approach is discussed in the context of the biosynthesis of JBIR-22 (and perhaps related natural products).

    UR - http://www.scopus.com/inward/record.url?scp=84946049693&partnerID=8YFLogxK

    UR - http://www.scopus.com/inward/citedby.url?scp=84946049693&partnerID=8YFLogxK

    U2 - 10.1039/c5ob01771h

    DO - 10.1039/c5ob01771h

    M3 - Article

    VL - 13

    SP - 10527

    EP - 10531

    JO - Organic and Biomolecular Chemistry

    JF - Organic and Biomolecular Chemistry

    SN - 1477-0520

    IS - 42

    ER -