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.
Synthesis of ketofuranosides by epoxidation-ring closure of enol ethers / A. BOSCHETTI, L. PANZA, F. RONCHETTI, G. RUSSO, L. TOMA. - In: JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS. I. - ISSN 0300-922X. - 1988:12(1988), pp. 3353-3357.
Synthesis of ketofuranosides by epoxidation-ring closure of enol ethers
F. RONCHETTI;G. RUSSOPenultimo
;
1988
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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