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

Research output: Contribution to journalArticle

Abstract

(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.

Original languageEnglish
Pages (from-to)1177-1179
Number of pages3
JournalSynthesis
Issue number10
Publication statusPublished - 1996

ASJC Scopus subject areas

  • Organic Chemistry

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    Amici, R., Pevarello, P., Colombo, M., & Varasi, M. (1996). Enantioselective synthesis of (S)-2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propanoic acid (S)-AMPA. Synthesis, (10), 1177-1179.