A New Route for the Oxidative Cleavage of Substituted Carbonylfurans as an Approach to 4-Oxobutanoic Acids

Abstract A novel approach to 4-oxobutanoic acids via the oxidative cleavage of 5-substituted 2-carbonylfurans is proposed. Optimization studies using various peroxide-based oxidation agents and other reaction conditions were performed. The obtained ketoacids have potential as precursors for synthesizing 4-substituted GABA analogues and racetams. The synthetic potential of γ-ketoacids was demonstrated through a series of transformations involving 4-oxo-4-(adamantan-1-yl)butanoic acid as the model substrate.