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  • Title: Stereoselective synthesis of 3-oxygenated-cis-dialkyl-2,5-substituted tetrahydrofurans from cyclohexadienediols.
    Author: Brovetto M, Seoane G.
    Journal: J Org Chem; 2008 Aug 01; 73(15):5776-85. PubMed ID: 18582114.
    Abstract:
    The 3-oxygenated-cis-dialkyl-2,5-substituted tetrahydrofuran system, present in several natural products, was prepared with good selectivity by acidic cyclization of 5-alkene-1,2,4-triol derivatives. The starting alkenol was obtained in few steps from a chiral cis-diol resulting from microbial oxidation of bromobenzene. The study of the cyclization allowed the rationalization of all experimental results by assuming a complete ionization at the allylic position and a model close to the one proposed by Labelle for homoallylic induction in five-membered ring closures.
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