An efficient diastereoselective strategy to access complex structural tetracycles was described through an organocascade quadruple reaction sequence between (E)‐2‐(3‐arylallylidene)‐1H‐indene‐1,3(2H)‐diones and β‐keto esters. The reaction proceeded through remote 1,6‐addition followed by sequential 1,4‐addition and aldol/aldol reactions to generate angularly‐fused carbocyclic motifs with favourable to excellent yields (up to 94%) and diastereoselectivities (up to >20:1 dr). An enantioselective organocascade approach was attempted to yield densely functionalized tetracycles containing seven chiral centres including a quaternary centre.magnified image