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  • Title: New strategy for the construction of a monotetrahydrofuran ring in Annonaceous acetogenin based on a ruthenium ring-closing metathesis: application to the synthesis of Solamin.
    Author: Prestat G, Baylon C, Heck MP, Grasa GA, Nolan SP, Mioskowski C.
    Journal: J Org Chem; 2004 Aug 20; 69(17):5770-3. PubMed ID: 15307756.
    Abstract:
    An original convergent total synthesis of Solamin (type A annonaceous acetogenin) was achieved. The central THF core was obtained by means of a ring-closing metathesis (RCM) reaction using a ruthenium imidazolylidene complex. The RCM substrate was prepared from a vinyl-substituted epoxide by reaction with an allyl alcohol, both synthesized from propargylic alcohol. The flexibility of the strategy should be useful in preparing various natural and unnatural annonaceous acetogenins.
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