In summary, we have developed a synthetic route to dimethyl cubane-1,4-dicarboxylate where the key photochemical [2+2] cycloaddition is catalysed by the cheap and widely available photosensitizer benzophenone to give near quantitative yields of the desired product 3 from dione 2. This allowed for the use of much lower energy light (λexc = 390 nm) than previous direct excitation methods that required a high-power Hg lamp or UV-B irradiation. Issues involving scale-up should be remedied using flow chemistry to allow for the photocatalysed [2+2] cycloaddition to be performed on a much larger scale. Finally, attempts at photocatalytic decarboxylation of 5 were attempted using conditions known to work for tertiary carboxylic acids; however, these were unsuccessful, with further work towards the photocatalytic functionalization of cubane derivatives ongoing.