The akuammiline alkaloids are complex monoterpene indole natural products with a rigid cage‐like architecture and diverse biological activities. Among them, strictamine has posed a longstanding synthetic challenge due to its congested quaternary carbon center and complex polycyclic framework. Herein, we report a concise formal synthesis of (±)‐strictamine enabled by a silylium‐catalyzed intramolecular (4 + 2) annulation with a donor–acceptor cyclobutane, delivering the target in 13 steps from tryptamine.