Enantiospecific Synthesis of (3S, 4S)-Statine and Its Analogue from D-Glucosamine as a Chiral Pool

The C(6)-carbon degradation and elimination of C(4)-hydroxy group of D-glucosamine were achieved in 8-steps and 30% overall yield to furnish (4R, 5S)-5-vinyl-2-oxazolidinone-4-carbaldehyde dimethyl acetal, which was utilized as a key intermediate for enantiospecific synthesis of biologically important threo β-hydroxy-γ-amino acids, natural (3S, 4S)-statine and (3S, 4S)-AHPPA