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[4-Iodo-3-(isopropylcarbamoyl)phenoxy]acetic acid was developed as a highly reactive and easily separable catalyst for the oxidative cleavage of tetrahydrofuran-2-methanols to γ-lactones in the presence of Oxone® (2KHSO5·KHSO4·K2SO4) as the co-oxidant. The reactivity of this new catalyst was considerably greater than that of our previously reported catalyst, 2-iodo-N-isopropylbenzamide. The new catalyst and product were easily separated by only liquid-liquid separation without chromatography. In addition, using a mixture of nitromethane and N,N-dimethylformamide as the solvent and heating enabled a low catalyst loading, a short reaction time, and high product yield. Oxidative cleavage using the new catalyst can be used as a practical and efficient method for synthesizing γ-lactones. [ABSTRACT FROM AUTHOR]

We previously reported a bifunctional organic catalyst that promotes highly efficient enantioselective halolactonizations of a broad array of olefinic acids. As part of that work, we demonstrated the desymmetrization of a prochiral substrate through a catalytic enantioselective halolactonization, and we report herein the application of one such desymmetrization process to the syntheses of F-ring subunit synthons of (+)-kibdelone C. [ABSTRACT FROM AUTHOR]