Synthesis of ketofuranosides by epoxidation-ring closure of enol ethers

Abstract
Z- and E-Hydroxy enol ethers, obtained from aldoses, either by an elimination reaction followed by a reduction or by a Wittig–Horner reaction, have been epoxidized using m-chloroperbenzoic acid or the Sharpless' procedure to afford ketofuranosides. The stereochemistry of both the epoxidation and the subsequent cyclization are discussed.

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