Enantioselective Synthesis of (S)-2-Amino-3-(3-Hydroxy-5-methylisoxazol-4-yl)propanoic Acid (S)-AMPA
作者:Raffaella Amici、Paolo Pevarello、Maristella Colombo、Mario Varasi
DOI:10.1055/s-1996-4357
日期:1996.10
(S)-AMPA (11) is an isoxazole containing α-amino acid used for selectively labeling the homonymous excitatory amino acid (EAA) receptor. Until now only enzymatic methods have been devised for its preparation. An asymmetric synthesis of (S)-AMPA is reported which exploits the formation of 3-bromo-4-hydroxymethyl-5-methylisoxazole intermediate 3 in a potassium fluoride promoted 1,3-dipolar cycloaddition and the application of the bislactim ether methodology for introducing the chiral α-amino acid center.