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

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    15 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

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    ASJC Scopus subject areas

    • Organic Chemistry
    • Physical and Theoretical Chemistry
    • Biochemistry

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