The synthesis of functionalised 6,7-dihydro-5H-indolo[2,1-a][2]benzazepine and 5,6,7,8-tetrahydroindolo[2,1-a][2]benzazocine from methyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylate, involving RCM as the key step to generate the tetracyclic indolo[2,1-a][2]benzazepine and indolo[2,1-a][2]benzazocine core structure, is outlined.