Asymmetric total synthesis of enantiopure (-)-methyl jasmonate via catalytic asymmetric intramolecular cyclopropanation of α-diazo-β-keto sulfone

Hiroyuki Takeda, Hideaki Watanabe, Masahisa Nakada

    Research output: Contribution to journalArticle

    35 Citations (Scopus)

    Abstract

    A new asymmetric total synthesis of enantiopure (-)-methyl jasmonate is described. This synthesis was accomplished starting from the new enantiopure building block prepared via the catalytic asymmetric intramolecular cyclopropanation (IMCP) of the α-diazo-β-keto 1-naphthyl sulfone, which was devised to give good selectivity both in the IMCP reaction and in the C-alkynylation of the intermediate required for the total synthesis of enantiopure (-)-methyl jasmonate.

    Original languageEnglish
    Pages (from-to)8054-8063
    Number of pages10
    JournalTetrahedron
    Volume62
    Issue number34
    DOIs
    Publication statusPublished - 2006 Aug 21

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    Sulfones
    methyl jasmonate

    Keywords

    • Catalytic asymmetric synthesis
    • Chiral building blocks
    • Intramolecular cyclopropanation
    • Total synthesis

    ASJC Scopus subject areas

    • Biochemistry
    • Organic Chemistry
    • Drug Discovery

    Cite this

    Asymmetric total synthesis of enantiopure (-)-methyl jasmonate via catalytic asymmetric intramolecular cyclopropanation of α-diazo-β-keto sulfone. / Takeda, Hiroyuki; Watanabe, Hideaki; Nakada, Masahisa.

    In: Tetrahedron, Vol. 62, No. 34, 21.08.2006, p. 8054-8063.

    Research output: Contribution to journalArticle

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