New methods for the rapid synthesis of complex heterocycles are of importance to the chemical community. In this presentation, the development and synthetic application of an intramolecular azomethine imine dipolar cycloaddition will be described. In situ generated azomethine imine 2 undergoes intramolecular cycloaddition to afford cyclopentapyrazolidine 3 in excellent yield with high diastereoselectivity. In a single step, one carbon−carbon bond, two five-membered rings, and three contiguous stereocenters are generated. Reaction optimization for substrates (e.g., 1) with alternative substitution at C2 and C7 will be disclosed. In addition, efforts to apply this methodology to the synthesis of oroidin-derived alkaloids will be presented.