Abstract
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 transfromations of β-oxy-α-diazo carbonyl compounds with sinthetic 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 led to an efficient synthesis of the natural aldonic acids KDG and DAH.
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