Abstract An expeditious route to methyl-7-oxo-1, 4, 5, 8-tetramethylbicyclo [3.3. 0] octane-3- carboxylate from a simple aromatic precursor is described. Oxidative dearomatization of 2- hydroxymethyl-3, 4, 6-trimethylphenol into spiroepoxycyclohexa-2, 4-dienone, its cycloaddition and triplet-sensitized 1, 2-acyl shift, and stereochemical inversion are the key features of our methodology.
