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
中村 紀雄
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ジャーナル フリー

1971 年 19 巻 1 号 p. 46-51

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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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