Stereoselective Alkylation of the Vinylketene Silyl N,O-Acetal and Its Application to the Synthesis of Mycocerosic Acid

Tatsuya Nakamura, Kei Kubota, Takanori Ieki, Seijiro Hosokawa

    Research output: Contribution to journalArticle

    10 Citations (Scopus)

    Abstract

    Stereoselective alkylation of the vinylketene silyl N,O-acetal possessing a chiral auxiliary has been achieved by using activated alkyl halides including allyl iodides, benzyl iodides, and propargyl iodide with Ag(I) ion in the presence of BF3·OEt2. The reaction proceeded to give reduced polyketides in high stereoselectivity. The synthesis of mycocerosic acid, a component of the cell envelope of Mycobacterium tuberculosis, has been accomplished by this methodology. During the synthetic studies, 2-methylbenzimidazole was found to be a bulky proton source which worked in the presence of liquid ammonia.

    Original languageEnglish
    Pages (from-to)132-135
    Number of pages4
    JournalOrganic Letters
    Volume18
    Issue number1
    DOIs
    Publication statusPublished - 2016 Jan 4

    Fingerprint

    acetals
    Acetals
    alkylation
    Alkylation
    Iodides
    iodides
    acids
    synthesis
    Polyketides
    tuberculosis
    liquid ammonia
    Stereoselectivity
    Cellular Structures
    Mycobacterium tuberculosis
    Ammonia
    halides
    Protons
    envelopes
    methodology
    Ions

    ASJC Scopus subject areas

    • Organic Chemistry
    • Physical and Theoretical Chemistry
    • Biochemistry

    Cite this

    Stereoselective Alkylation of the Vinylketene Silyl N,O-Acetal and Its Application to the Synthesis of Mycocerosic Acid. / Nakamura, Tatsuya; Kubota, Kei; Ieki, Takanori; Hosokawa, Seijiro.

    In: Organic Letters, Vol. 18, No. 1, 04.01.2016, p. 132-135.

    Research output: Contribution to journalArticle

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