Preparation of chiral building blocks for the enantioselective total synthesis of ent-kauranoids by the pig liver esterase-catalyzed asymmetric hydrolysis of a dialkyl malonate-type prochiral diester

Yuji Namiki, Tomohiro Fujii, Masahisa Nakada

    Research output: Contribution to journalArticle

    7 Citations (Scopus)

    Abstract

    The preparation of chiral building blocks, suitable for use in the enantioselective total synthesis of kauranoids and ent-kauranoids, is reported herein. The pig liver esterase-catalyzed asymmetric hydrolysis of dimethyl 3,3-dimethyl-2-methylenecyclohexane-1,2-dicarboxylate, a malonate-type prochiral diester, afforded the corresponding half-ester in 96% yield and with 99% enantiomeric excess. The absolute configuration of the half-ester was determined by X-ray crystallographic analysis of its derivative and its enantiodivergent transformations are also described herein.

    Original languageEnglish
    Pages (from-to)718-724
    Number of pages7
    JournalTetrahedron Asymmetry
    Volume25
    Issue number9
    DOIs
    Publication statusPublished - 2014 May 15

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    swine
    Esterases
    liver
    Liver
    hydrolysis
    esters
    Hydrolysis
    Esters
    preparation
    synthesis
    Derivatives
    X rays
    configurations
    x rays
    malonic acid

    ASJC Scopus subject areas

    • Organic Chemistry
    • Inorganic Chemistry
    • Physical and Theoretical Chemistry
    • Catalysis

    Cite this

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    abstract = "The preparation of chiral building blocks, suitable for use in the enantioselective total synthesis of kauranoids and ent-kauranoids, is reported herein. The pig liver esterase-catalyzed asymmetric hydrolysis of dimethyl 3,3-dimethyl-2-methylenecyclohexane-1,2-dicarboxylate, a malonate-type prochiral diester, afforded the corresponding half-ester in 96{\%} yield and with 99{\%} enantiomeric excess. The absolute configuration of the half-ester was determined by X-ray crystallographic analysis of its derivative and its enantiodivergent transformations are also described herein.",
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    AU - Fujii, Tomohiro

    AU - Nakada, Masahisa

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    AB - The preparation of chiral building blocks, suitable for use in the enantioselective total synthesis of kauranoids and ent-kauranoids, is reported herein. The pig liver esterase-catalyzed asymmetric hydrolysis of dimethyl 3,3-dimethyl-2-methylenecyclohexane-1,2-dicarboxylate, a malonate-type prochiral diester, afforded the corresponding half-ester in 96% yield and with 99% enantiomeric excess. The absolute configuration of the half-ester was determined by X-ray crystallographic analysis of its derivative and its enantiodivergent transformations are also described herein.

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