An expedient route to access the functionalized structural core of aflavinines has been developed starting from three readily available fragments over 12 steps in 29.1% overall yield without using any transition metal catalysis. The key feature of this approach is a tandem intramolecular Diels–Alder cycloaddition to complete the hexacyclic framework with the correct stereochemistry and all the requisite structural elements in place to achieve the total synthesis of aflavinine and its congeners.