Reactions of monosaccharide derivatives with diazocarbonyl compounds. Reactivity and synthetic applications

Article abstract of DOI:10.1016/S0040-4020(98)00369-X

The reaction of monosaccharide derivatives with different stabilized diazo compounds is reported. Studies on the reactivity of the condensation products have been undertaken, finding out novel transformations of β-oxy- α-diazo carbonyl compounds with synthetic applications. Thus, a stereoselective Wolff rearrangement provided syn 2-hydroxy-1-methyl compounds, which represent macrolide type structural subunits. On the other hand, rhodium (II) mediated rearrangements of β-acetoxy-α-diazo carbonyl compounds derived from monosaccharides have loci to an efficient synthesis of the natural aldonic acids KDG and DAH.