We have achieved the divergent total synthesis of four kopsane alkaloids which share a complex heptacyclic caged ring system. Key transformations include an asymmetric Diels-Alder reaction to assemble the central bicyclo[2.2.2]octane moiety and the quaternary stereocenter at C20, a SmI(2) -mediated cascade reduction/aldol reaction to construct the five-membered ring and the quaternary stereocenter at C7, and a late-stage cascade reductive amination/cyclization to establish the highly strained caged ring system. CI - (c) 2022 Wiley-VCH GmbH.