Asymmetric synthesis of (2 S,3 R) β-(4-F-3-NO 2) phenyl serine, D-( R)-4-methoxy-3,5-bis tbutyldimethylsiloxy phenylglycine and their assemblage to C-O-D ring of vancomycin

Abstract

The asymmetric synthesis of two appropriately functionalized 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 biaryl ether formation via intramolecular S NAr reaction led to the fully functionalized C-O-D ring of vancomycin.