Stereoselective acylation of the E, e -vinylketene silyl N, O -acetal and its application to the synthesis of khafrefungin

Yuta Takahashi, Maiko Otsuka, Mio Harachi, Yuki Mukaeda, Seijiro Hosokawa

    Research output: Contribution to journalArticle

    14 Citations (Scopus)

    Abstract

    Stereoselective acylation of the E,E-vinylketene silyl N,O-acetal possessing a chiral auxiliary has been achieved by using acid anhydrides and SnCl4. Acid anhydrides having alkyl chains gave the adducts in excellent stereoselectivity. The formal synthesis of khafrefungin has been accomplished by the methodology.

    Original languageEnglish
    Pages (from-to)4106-4109
    Number of pages4
    JournalOrganic Letters
    Volume16
    Issue number16
    DOIs
    Publication statusPublished - 2014 Aug 15

    Fingerprint

    acylation
    acetals
    Acylation
    Acetals
    Anhydrides
    anhydrides
    Stereoselectivity
    acids
    Acids
    synthesis
    adducts
    methodology
    khafrefungin
    stannic chloride

    ASJC Scopus subject areas

    • Organic Chemistry
    • Physical and Theoretical Chemistry
    • Biochemistry

    Cite this

    Stereoselective acylation of the E, e -vinylketene silyl N, O -acetal and its application to the synthesis of khafrefungin. / Takahashi, Yuta; Otsuka, Maiko; Harachi, Mio; Mukaeda, Yuki; Hosokawa, Seijiro.

    In: Organic Letters, Vol. 16, No. 16, 15.08.2014, p. 4106-4109.

    Research output: Contribution to journalArticle

    Takahashi, Yuta ; Otsuka, Maiko ; Harachi, Mio ; Mukaeda, Yuki ; Hosokawa, Seijiro. / Stereoselective acylation of the E, e -vinylketene silyl N, O -acetal and its application to the synthesis of khafrefungin. In: Organic Letters. 2014 ; Vol. 16, No. 16. pp. 4106-4109.
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