We describe a novel strategy for the synthesis of N-substituted nortropinone derivatives starting from tropinone. The key step of our synthesis is a reactivity umpolung of tropinone, which yields 8, 8-dimethyl-3-oxo-8-azonia-bicyclo [3.2. 1] octane iodide (IDABO) as a stable and convenient synthetic equivalent of cycloheptadienone.