Stereoselective Synthesis of Tabtoxinine-β-lactam by Using the Vinylogous Mukaiyama Aldol Reaction with Acetate-Type Vinylketene Silyl N,O-Acetal and α-Keto-β-lactam

Hirotaka Ejima, Fumihiro Wakita, Ryo Imamura, Takuya Kato, Seijiro Hosokawa

    Research output: Contribution to journalArticle

    8 Citations (Scopus)

    Abstract

    Stereoselective total synthesis of tabtoxinine-β-lactam has been achieved. The vinylogous Mukaiyama aldol reaction with vinylketene silyl N,O-acetal and α-keto-β-lactam proceeded to afford the adduct possessing a TβL-skeleton with a tert-alcohol in high yield and stereoselectivity. Stereoselective introduction of the amino group has been accomplished by azidation at the α position of the imide followed by hydrogenolysis. A straightforward method to achieve the potent inhibitor of glutamine synthetase, possessing both α-hydroxy-β-lactam and α-amino acid moieties, has been established.

    Original languageEnglish
    Pages (from-to)2530-2532
    Number of pages3
    JournalOrganic Letters
    Volume19
    Issue number10
    DOIs
    Publication statusPublished - 2017 May 19

    Fingerprint

    glutamine
    Lactams
    acetals
    hydrogenolysis
    Acetals
    imides
    musculoskeletal system
    inhibitors
    adducts
    amino acids
    acetates
    Acetates
    alcohols
    synthesis
    Imides
    Stereoselectivity
    Glutamate-Ammonia Ligase
    Hydrogenolysis
    Skeleton
    Alcohols

    ASJC Scopus subject areas

    • Biochemistry
    • Physical and Theoretical Chemistry
    • Organic Chemistry

    Cite this

    Stereoselective Synthesis of Tabtoxinine-β-lactam by Using the Vinylogous Mukaiyama Aldol Reaction with Acetate-Type Vinylketene Silyl N,O-Acetal and α-Keto-β-lactam. / Ejima, Hirotaka; Wakita, Fumihiro; Imamura, Ryo; Kato, Takuya; Hosokawa, Seijiro.

    In: Organic Letters, Vol. 19, No. 10, 19.05.2017, p. 2530-2532.

    Research output: Contribution to journalArticle

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    AU - Wakita, Fumihiro

    AU - Imamura, Ryo

    AU - Kato, Takuya

    AU - Hosokawa, Seijiro

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