A 14‐step synthesis of (+)‐cochlearol B is reported. This renoprotective meroterpenoid features a unique core structure containing a densely substituted cyclobutane ring with three stereocenters. Our strategy employed an organocatalytic Kabbe condensation in route to the key chromenyl triflate. A subsequent Catellani reaction incorporated the remaining carbon atoms featured in the skeleton of cochlearol B. An ensuing visible‐light‐mediated 2+2 photocycloaddition closed the cyclobutane and formed the central bicyclo3.2.0heptane core. Notably, careful design and tuning of the Catellani and photocycloaddition reactions proved crucial in overcoming undesired reactivity, including cyclopropanation reactions and 4+2 cycloadditions. A 14‐step approach to (+)‐cochlearol B is reported. The strategy involves an organocatalytic Kabbe condensation, Catellani reaction, and visible‐light‐mediated 2+2 cycloaddition to rapidly access the core of this natural product. Careful design and tuning of the Catellani and photocycloaddition reactions proved crucial in overcoming undesired reactivity, including cyclopropanation reactions, and 4+2 cycloadditions.