Streamlined biomimetic synthesis of paracaseolide A via aerobic oxidation of a 2-silyloxyfuran

A simple, bioinspired synthesis of the naturally occurring Cdc25B inhibitor paracaseolide A is reported. Key steps include: (i) an aerobic oxidation of a 2-silyloxyfuran to the corresponding silyl ketoester, and (ii) the preparation of the former intermediate by silylation of an α-alkylidenebutenolide. Both of these high-yielding transformations are unprecedented.