Spirooxindole and iminoindoline structures can be found in a wide range of complex natural products, and compounds containing these groups invariably display interesting biological activities. Considering their interesting biological properties and complex architecture, significant research efforts have been directed towards developing new synthetic methods for constructing these structures. This review summarizes our studies towards developing novel synthetic strategies capable of accessing these structures, as well as the applications of these methods to synthesizing natural products, including elacomine and dehaloperophoramidine.