Herein, we report a biomimetic oxidative coupling cyclization strategy for the highly efficient functionalization of tetrahydrocarbolines (THCs). This process enables rapid access to complex isochromanoindolenine scaffolds in moderate to excellent yields. The reaction proceeds smoothly and rapidly (complete within minutes) in an open flask. This operationally simple protocol is scalable and compatible with a wide range of functional groups. Late-stage functionalization of a pharmacologically relevant molecule is also demonstrated.