Enantioselective total synthesis of (+)-colletoic acid via catalytic asymmetric intramolecular cyclopropanation of an α-diazo-β-keto diphenylphosphine oxide

Takashi Sawada, Masahisa Nakada

    Research output: Contribution to journalArticle

    28 Citations (Scopus)

    Abstract

    The enantioselective total synthesis of (+)-colletoic acid, a potent naturally occurring 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) inhibitor, is described. This total synthesis features a highly enantioselective catalytic asymmetric intramolecular cyclopropanation of an α-diazo-β-keto diphenylphosphine oxide and five highly stereoselective reactions (cyclopropane opening, Diels-Alder reaction, iodolactonization, alkene formation, and reduction of α,β-unsaturated carboxylic acid).

    Original languageEnglish
    Pages (from-to)1004-1007
    Number of pages4
    JournalOrganic Letters
    Volume15
    Issue number5
    DOIs
    Publication statusPublished - 2013

    Fingerprint

    11-beta-Hydroxysteroid Dehydrogenases
    Cycloaddition Reaction
    Alkenes
    Carboxylic Acids
    Diels-Alder reactions
    acids
    cyclopropane
    dehydrogenases
    oxides
    synthesis
    carboxylic acids
    inhibitors
    alkenes
    colletoic acid
    triphenylphosphine oxide

    ASJC Scopus subject areas

    • Organic Chemistry
    • Physical and Theoretical Chemistry
    • Biochemistry

    Cite this

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    abstract = "The enantioselective total synthesis of (+)-colletoic acid, a potent naturally occurring 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) inhibitor, is described. This total synthesis features a highly enantioselective catalytic asymmetric intramolecular cyclopropanation of an α-diazo-β-keto diphenylphosphine oxide and five highly stereoselective reactions (cyclopropane opening, Diels-Alder reaction, iodolactonization, alkene formation, and reduction of α,β-unsaturated carboxylic acid).",
    author = "Takashi Sawada and Masahisa Nakada",
    year = "2013",
    doi = "10.1021/ol303459x",
    language = "English",
    volume = "15",
    pages = "1004--1007",
    journal = "Organic Letters",
    issn = "1523-7060",
    publisher = "American Chemical Society",
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    T1 - Enantioselective total synthesis of (+)-colletoic acid via catalytic asymmetric intramolecular cyclopropanation of an α-diazo-β-keto diphenylphosphine oxide

    AU - Sawada, Takashi

    AU - Nakada, Masahisa

    PY - 2013

    Y1 - 2013

    N2 - The enantioselective total synthesis of (+)-colletoic acid, a potent naturally occurring 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) inhibitor, is described. This total synthesis features a highly enantioselective catalytic asymmetric intramolecular cyclopropanation of an α-diazo-β-keto diphenylphosphine oxide and five highly stereoselective reactions (cyclopropane opening, Diels-Alder reaction, iodolactonization, alkene formation, and reduction of α,β-unsaturated carboxylic acid).

    AB - The enantioselective total synthesis of (+)-colletoic acid, a potent naturally occurring 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) inhibitor, is described. This total synthesis features a highly enantioselective catalytic asymmetric intramolecular cyclopropanation of an α-diazo-β-keto diphenylphosphine oxide and five highly stereoselective reactions (cyclopropane opening, Diels-Alder reaction, iodolactonization, alkene formation, and reduction of α,β-unsaturated carboxylic acid).

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    U2 - 10.1021/ol303459x

    DO - 10.1021/ol303459x

    M3 - Article

    VL - 15

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    EP - 1007

    JO - Organic Letters

    JF - Organic Letters

    SN - 1523-7060

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    ER -