The synthesis of the [2.2. 2]-bicyclic core (23) of the neurotrophic factor 11-O- debenzoyltashironin (1) has been achieved by an oxidative dearomatization-transannular Diels–Alder cascade. We have shown that the reaction sequence is also valuable for the efficient construction of related, complex [2.2. 2]-bicyclic compounds (vide infra).