Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
The Improved Syntheses of dl-Ibotenic Acid and Muscimol
NORIO NAKAMURA
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1971 Volume 19 Issue 1 Pages 46-51

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Abstract

dl-Ibotenic acid (I) was synthesized in a better yield than the known methods, starting from diethyl 3-chloroglutaconate (VII). Reaction of VII with hydroxylamine in the presence of sodium hydroxide followed by esterification afforded ethyl 3-hydroxy-5-isoxazoleacetate (IV), which was, after benzenesulfonylation, brominated with NBS to ethyl α-bromo-3-benzenesulfonyloxy-5-isoxazoleacetate (X). Hydrolysis and treatment with ammonia of X gave I. Synthesis of muscimol (II) from IV was also described.

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© The Pharmaceutical Society of Japan
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