K. Shinozaki, Kazuhiro Mizuno, H. Oda
Jun 1, 1996
Citations
0
Influential Citations
5
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
Biologically important threo-β-hydroxy-γ-amino acids, (3S,4S)-statine ((3S,4S)-4-amino-3-hydroxy-6-methylheptanoic acid) (1) and (3S,4S)-AHPPA (3S,4S)-4-amino-3-hydroxy-5-phenylpentanoic acid) (2), were synthesized starting from D-glucosamine (3) as a chiral pool. Two routes for the transformation of D-glucosamine to key intermediates, which are applicable to the synthesis of threo-β-hydroxy-γ-amino acids, were investigated. The successful route involved C(6)-carbon degradation and elimination of the C(4)-hydroxy group of D-glucosamine in 8 steps and 30% overall yield to furnish (4R,5S)-2-oxo-5-vinyloxazolidine-4-carbaldehyde dimethyl acetal (17), which has been utilized as a versatile intermediate for synthesizing the target compounds.