Rearranged cage ketones 6a and 6b are reported in eight linear synthetic steps from 2,5‐dimethoxybenzaldehyde 9 without the use of protecting groups. In this regard, Diels–Alder reaction, [2+2]photocycloaddition and Lewis acid promoted rearrangement with BF3·OEt2 were used as key steps. Surprisingly, during the ring expansion process with Lewis acid, solvent incorporation occurred. This rearrangement approach has provided difficult complex targets through non‐obvious synthetic routes. The rearrangement process demonstrated here opens up a new synthetic strategy to interesting and unusual cage molecules.