Abstract An efficient route to prepare the 4-hydroxy-2, 3, 4, 5-tetrahydro [1, 4] diazepino [1, 2- a] indol-1-one scaffold is described. The key reactions of the synthesis are an iodolactonisation followed by a lactone-to-lactam rearrangement. Various 11-substituted derivatives were obtained by palladium-mediated cross-coupling reactions.