Herein, we report the concise total syntheses of (+)-leucolusine and (-)-7-epi-leucolusine achieved in 8 steps starting from commercially available piperidin-2-one. Our strategy highlights a palladium-catalyzed decarboxylative asymmetric allylic alkylation for constructing the δ-lactam bearing a C20 all-carbon quaternary stereocenter. Additionally, the cis-fused octahydrofuro[2,3-b]pyridine unit was efficiently constructed via a one-pot protocol encompassing reduction and oxa-Mannich-type cyclization processes.