104324-18-7Relevant articles and documents
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
Zhu, Jieping,Bouillon, Jean-Philippe,Singh, Girij Pal,Chastanet, Jacqueline,Beugelmans, Rene
, p. 7081 - 7084 (2007/10/02)
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 SNAr reaction led to the fully functionalized C-O-D ring vancomycin.
Asymmetric Glycine Enolate Aldol Reactions: Synthesis of Cyclosporine's Unusual Amino Acid, MeBmt
Evans, David A.,Weber, Ann E.
, p. 6757 - 6761 (2007/10/02)
The chiral glycine synthon, 3c, as its derived stannous enolate, has been demonstrated to undergo a highly syn diastereoselective aldol addition reaction with representative aldehydes to give the adducts 5 (R = C6H5, Me, Me2CH) in yields ranging from 71 to 92percent.The utility of these intermediates has been demonstrated via the subsequent three-step transformation of these adducts to the enantiomerically pure N-methyl β-hydroxy amino acids 1.This reaction methodology has been applied to the asymmetric synthesis of (4R)-4-((E)-2-butenyl)-4,N-dimethyl-L-threonine (1a), an important constituent in the immunosuppressant peptide cyclosporine.Several additional structural analogues of 1a were also prepared in conjunction with this study.
