Studies on Acetylenic Compounds. XLIII. Synthesis of Ibotenic Acid.
- 1 January 1967
- journal article
- research article
- Published by Pharmaceutical Society of Japan in CHEMICAL & PHARMACEUTICAL BULLETIN
- Vol. 15 (7) , 1025-1031
- https://doi.org/10.1248/cpb.15.1025
Abstract
Ibotenic acid ([alpha]-amino-[beta]-hydroxy-5-isoxazoleacetic acid monohydrate) (I), a flycidal amino acid isolated from Amanitae fungi, was synthesized. The reaction of ethyl 4,4-diethoxytetrolate with hydroxylamine in the presence of alkali gave 3-hydroxy-5-isoxazolecarboxaldehyde diethyl acetal which was hydrolyzed with 50% AcOH to the corresponding 3-hydroxy-5-isoxazolecarboxaldehyde (n). Strecker or Bucherer reaction of II followed by alkaline hydrolysis afforded I, which was identical with the natural ibotenic acid.This publication has 0 references indexed in Scilit: