Asymmetric synthesis of (2S,3R) beta -(4-F-3-NO2) phenyl serine, D-(R)-4-methoxy-3,5-bistbutyldimethylsiloxy phenylglycine and their assemblage to C-O-D ring of vancomycin

The asym. synthesis of two appropriately functionalized nonproteinogenic amino acids I (Troc = CO2CH2CCl3, TBS = SiMe2CMe3) and II (Boc = Me3CO2C) needed for the total synthesis of vancomycin is described. The assemblage of these amino acids into linear tripeptide followed by biaryl ether formation via intramol. SNAr reaction led to the fully functionalized C-O-D ring III of vancomycin. [on SciFinder (R)]