80601-61-2Relevant academic research and scientific papers
Use of β-Ketocarboxylic Acids for Syntheses of 6-Substituted 4-Hydroxy-2-pyrones and Acyclic β-Diketones
Ohta, Shunsaku,Tsujimura, Atsuhiko,Okamoto, Masao
, p. 2762 - 2768 (2007/10/02)
β-Ketocarboxylic acids including β-ketoglutaric acid half-esters were cyclized by treating them with 1,1'-carbonyl-diimidazole to give 6-substituted 3-acyl-4-hydroxy-2-pyrones in good yields. 5-Aryl-3,5-dioxo-1-pentanoic acid and monomethyl malonate gave 6-aryl-4-hydroxy-2-pyrone and dimethyl β-ketoglutarate, respectively, on similar treatment.Anibin, one of the Aniba alkaloids, was synthesized from 5-(3-pyridyl)-4-hydroxy-2-pyrone.In addition, it was confirmed that reaction of magnesium β-ketocarboxylate with acylimidazolide gave the corresponding acyclic β-diketone in excellent yield.Keywords - β-ketocarboxilic acid; biogenetic-type synthesis; 4-hydroxy-2-pyrone; β-polyketide; β-ketoglutaric acid; dehydroacetic acid; anibin; Aniba alkaloid; 3-acyl-4-hydroxy-2-pyrone; β-diketone.
