An enyne metathesis/(4 + 2)-dimerization route to (±)-differolide

Thomas R. Hoye, Scott M. Donaldson, Tricia J. Vos

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(equation presented) A concise total synthesis of (±)-differolide (1) has been achieved. 2-Vinylbutenolide (2) was prepared by enyne metathesis of allyl propynoate (3) usinq the Grubbs initiator 4. This reaction was examined by 1H NMR spectroscopy, which led to the hypothesis that low concentration of ruthenium species and high concentration of enyne substrate would be advantageous. Accordingly, slow addition of 4 to solutions of enyne 3 was found to be beneficial. Spontaneous dimerization of 2 gave (±)-differolide (1) and an isomer.

Original languageEnglish (US)
Pages (from-to)277-279
Number of pages3
JournalOrganic Letters
Issue number2
StatePublished - Jul 29 1999


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