A practical diastereoselective method for the synthesis of benzoannelated tri- and tetracyclic bridged sultams has been developed. The synthetic route employs widely available, substituted -iodoanilines and is based on intramolecular Michael addition followed by cycloalkylation with dihaloalkanes, or vice versa. The target compounds were isolated in good yields and the diastereoselectivity of the reaction could be easily controlled by the order of Michael addition and cycloalkylation steps.