As a model study for the synthesis of anisatin, 2-oxaspiro [3.5] nonane and 5-hydroxy-5- methyl-2-oxaspiro [3.5] nonane were synthesized from methyl cyclohexanecarboxylate and 2-ethoxycarbonylcyclohexanone, respectively, and these oxetanes were submitted to ruthenium tetroxide oxidation to afford the corresponding β-lactones.