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

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

Istituto Europeo di Oncologia

Research output: Contribution to journal › Article › peer-review

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 language	English
Pages (from-to)	1177-1179
Number of pages	3
Journal	Synthesis
Issue number	10
Publication status	Published - 1996

ASJC Scopus subject areas

Organic Chemistry

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title = "Enantioselective synthesis of (S)-2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propanoic acid (S)-AMPA",

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.",

author = "Raffaella Amici and Paolo Pevarello and Maristella Colombo and Mario Varasi",

year = "1996",

language = "English",

pages = "1177--1179",

journal = "Synthesis",

issn = "0039-7881",

publisher = "Georg Thieme Verlag",

number = "10",

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T1 - Enantioselective synthesis of (S)-2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propanoic acid (S)-AMPA

AU - Amici, Raffaella

AU - Pevarello, Paolo

AU - Colombo, Maristella

AU - Varasi, Mario

PY - 1996

Y1 - 1996

N2 - (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.

AB - (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.

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M3 - Article

AN - SCOPUS:0029809205

SP - 1177

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JO - Synthesis

JF - Synthesis

SN - 0039-7881

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ER -

Enantioselective synthesis of (S)-2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propanoic acid (S)-AMPA

Abstract

ASJC Scopus subject areas

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