A Concise Conversion of Glucose to Chiral Erythrose Derivative and a Stereospecific Synthesis of 3-Amino-4-cyclohexyl-2-hydroxybutanoates

Inokuchi, T.; Tanigawa, S.; Kanazaki, M.; Torii, S. Synlett 1991, 707.

Electrooxidation of a D-glucose derivative followed by Baeyer-Villiger oxidation leads to an erythrose derivative. Thus cyclohexylnorstatines 11 are derived from D-glucose in about 10% overall yield via cyclohexylation at the C(6) position, azidation at the C(5) carbon, and cleavage of the C(2)-C(3) bond by the electrooxidation/Baeyer-Villiger oxidation sequence.