A new synthetic route for a short synthesis of (±)-leuconodines D and E was developed. The rapid construction of the diaza[5.5.6.6]fenestrane core was achieved through a sequence involving a Pd-catalyzed aerobic oxidative Heck cross-coupling reaction for the construction of indole δ-lactam containing a full-carbon quaternary center, an epoxidative cyclization for the assembly of pyrroloindole, and a ring-closing metathesis for the construction of the piperidine ring. As a result, the total synthesis of (±)-leuconodine E (2) was achieved for the first time within a 10-step linear sequence, and a more concise total synthesis of (±)-leuconodine D (1) was accomplished within a 12-step linear sequence from the commercially available tryptophol.