Asymmetric Synthesis of (2S,3R) β-(4-F-3-NO2) phenyl Serine, D-(R)-4-methoxy-3,5-Bis tButyldimethylsiloxy Phenylglycine and Their Assemblage to C-O-D Ring of Vancomycin

Article abstract of DOI:10.1016/0040-4039(95)01409-B

The asymmetric synthesis of two appropriately functionalyzed non-proteinogenic amino acids 2 and 3 needed for the total synthesis of vancomycin was described.The assemblage of these amino acids into linear tripeptide followed by biary ether formation via intramolecular S_NAr reaction led to the fully functionalized C-O-D ring vancomycin.