Abstract
The mode of reduction of Lg(+)-oxime (II) was utilized for conversion of Lg(+)-threo-(I) to Dg(-)-threo-(I). Dg(+)-erythro-(V) was prepared by the known method and cyclized by acetone to Dg(+)-erythro-(I), whose oxidation with perbenzoic acid afforded chiefly Dg(-)-erythro-nitroso-dimer (XVII) and a small amount of Dg(+)-oxime (II) as a by-product. Thermal depolymerization of the nitroso-dimer (XVII) afforded Dg(+)-oxime (II) which was reduced under high pressure to Dg(-)-threo-(I). The mechanism of oxidation of threo-(I) and erythro-(I) with perbenzoic acid was assumed to be controlled by the conformation of the nitroso compound (XVI) formed as an intermediate.
