γ-Hydroxybutenolides command considerable attention on account of their significant biological properties and growing utilization as synthetic intermediates. In the course of a biomimetic total synthesis of the Cdc25B inhibitor paracaseolide A, we were pleasantly surprised to discover that in the presence of traces of a Brønsted acid, 2-silyloxyfurans undergo facile oxidation with molecular oxygen (or air) to furnish silyl ketoesters, which can be isolated, or directly subjected to acidic hydrolysis affording γ-hydroxybutenolides. The mechanism and scope of this inherently green transformation, along with efforts directed at the synthesis of other natural product targets, will be discussed.

Green and scalable synthesis of γ-hydroxybutenolides via aerobic oxidation of 2-silyloxyfurans

249th National Meeting (2015)

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