The reaction of alkynyl Fischer carbenes and isobenzofurans gives rise to the corresponding [4 + 2] cycloadducts. The newly formed carbeneadducts are suitable for benzannulation processes in the presence of tert-butylisocyanide or carbon monoxide to yield a variety of new highlysubstituted polycyclic structures having the anthraquinone framework. The whole two-step process is conducted in a one-pot fashion fromeasily available 1,4-dihydro-1,4-epoxynaphthalenes.