A highly efficient cascade cyclization of phenidones and enynones has been developed via a Ru(II)-catalyzed C-H activation initiated indole formation/Diels-Alder reaction/iminium ion cyclization sequence, which afforded hexacyclic indolines as single diastereomer in good to excellent yields with a broad substrate scope under mild conditions. The reaction features the simultaneous generation of five new chemical bonds and four new rings in one pot, providing a rapid and concise approach toward polycyclic indoline alkaloids and their analogues.