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Treatment of bicyclic lactones derived from Diels-Alder reactions of 3-carbomethoxy-2-pyrone under radical conditions leads to a series of interesting skeletal rearrangements. The stereochemical and optical integrity of the starting material are maintained throughout the process.

The skeletal rearrangement of bicyclo[2.2.2]lactones, involving a mild and chemoselective palladium-catalysed translocation key-step, provides an efficient and diastereoselective access to synthetically useful bicyclo[3.3.0]lactones.

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