Ibotenic acid (α-amino-3-hydroxy-5-isoxazoleacetic acid monohydrate) (I), a flycidal amino acid isolated from Amanitae fungi, was synthesized. The reaction of ethyl 4, 4-diethoxytetrolate (V) with hydroxylamine in the presence of alkali gave 3-hydroxy-5-isoxazolecarboxaldehyde diethyl acetal (VI), which was hydrolyzed with 50% AcOH to the corresponding 3-hydroxy-5-isoxazolecarboxaldehyde (II). Strecker or Bucherer reaction of II followed by alkaline hydrolysis afforded I, which was identical with the natural ibotenic acid.
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Kishida et al. (1967) studied this question.