Cephanolides A-D are cephalotane-type diterpenoids featuring a novel 6/6/6/5 tetracyclic core embedded with a bridged δ-lactone. The asymmetric and divergent total syntheses of cephanolides A-D have been accomplished, proceeding in 11-14 steps from a known alcohol. The salient features of the present work include (i) a substrate-controlled diastereoselective intermolecular Diels-Alder reaction to form the 6-6 cis-fused rings, (ii) a palladium-catalyzed formal bimolecular [2 + 2 + 2] cycloaddition reaction via a partially intermolecular cascade reaction sequence involving multiple carbometalations to rapidly install the key tetracyclic skeleton, and (iii) lactonization and late-stage oxidative diversification to complete total syntheses of the four benzenoid cephanolides.