An efficient amino acid-/self-/base-/ruthenium-/thermal-catalyzed two-step process for the synthesis of functionalized drug-like carbocycles was achieved through combinations of cascade TCRA/C-allylation/enyne-RCM/Diels–Alder reactions as key steps starting from simple acyclic substrates. In this communication, we report the two-step synthesis of drug-like carbocycles through a combination of organocatalysis with ruthenium-catalysis.