We developed a method employing stoichiometric meta-chloroperbenzoic acid (m-CPBA) as an oxidant and hydrogen fluoride pyridine (pyr·HF) as a fluoride source with catalytic amounts of iodobenzene (PhI) for the cyclization and fluorination–dearomatization of phenols, leading to a range of fluorocyclohexa-dienones with yields of up to 94%. This reaction provides a convenient method to synthesize fluorine-containing dehydroaltenusin analogs under mild conditions, and without expensive reagents. These analogs have potential application as inhibitors of DNA polymerase.