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Synthesis of ketofuranosides by epoxidation-ring closure of enol ethers

  • Anna Boschetti
  • , Luigi Panza
  • , Fiamma Ronchetti
  • , Giovanni Russo
  • , Lucio Toma

Research output: Contribution to journalArticlepeer-review

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.

Original languageEnglish
Pages (from-to)3353-3365
Number of pages13
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number12
DOIs
Publication statusPublished - 1988
Externally publishedYes

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