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Synthesis 1996; 1996(10): 1177-1179
DOI: 10.1055/s-1996-4357
short paper
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Enantioselective Synthesis of (S)-2-Amino-3-(3-Hydroxy-5-methylisoxazol-4-yl)propanoic Acid (S)-AMPA

Raffaella Amici, Paolo Pevarello* , Maristella Colombo, Mario Varasi
  • *Pharmacia & Upjohn, R & D-CNS, Medicinal Chemistry Department and R & D-Analytical Chemistry, Via per Pogliano, I-20014 Nerviano (MI), Italy, Fax +39(331)583012; E-Mail paolo.pevarello@eu.pnu.com
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Publikationsdatum:
31. Dezember 2000 (online)

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(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.

1,3-dipolar cycloaddition - bromonitrile oxide - isoxazole - Schöllkopf method - (S)-AMPA