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

Zhu, JiepingBouillon, Jean-PhilippeSingh, Girij Pal2010-11-252010-11-252010-11-25199510.1016/0040-4039(95)01409-Bhttps://infoscience.epfl.ch/handle/20.500.14299/58565The 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)]Asymmetric synthesis and induction (asym. synthesis of protected [fluoro(nitro)phenyl]serine and protected [methoxy(dihydroxy)phenyl]glycine and their assemblage to C-O-D ring of vancomycin)vancomycin ring fragment asym synthesis; phenylserine protected fluoronitro asym synthesis; fluoronitrophenylserine protected asym synthesis; methoxydihydroxyphenylglycine protected asym synthesis; phenylglycine protected methoxydihydroxy asym synthesisAsymmetric 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 vancomycintext::journal::journal article::research article