Synthesis of Medium and Large Ring Compounds, XLI Synthesis and Reactions of Optically Active Bridged Methyl Deoxyfuranosides

Abstract

AbstractThe resolution of the earlier reported racemic bridged methyl deoxyfuranosides 1 and 3 was achieved via fractional crystallization of the ephedrinium salts 2 or by column chromatography of the camphanoates 5. The absolute configurations of 1 and 3 were established by X‐ray structural analysis of the (S)‐α‐naphthylethylammonium carboxylate (+)‐4 and by correlation with the other enantiomerically pure compounds of this type. (+)‐3 was converted into the 2,5‐bridged altrose derivative (+)‐8.