Condensation of 11-7 to form oxime coupling partner 10-2 with O-benzoylhydroxylamine or related hydroxylamines were unsuccessful, and provided complex mixtures of products. The side products may arise as a result of competitive aza-Michael and other side pathways due to the highly electrophilic enone β-position. Various additional strategies to reach 10-2 were also investigated unsuccessfully, including formation of an isoxazole or Michaelis-Arbuzov rearrangement on the α-bromo oxime and subsequent Horner-Wadsworth-Emmons reaction. Due to the challenge of synthesizing the exocyclic α,β-unsaturated oxime (10-2), alternative strategies for the formation of the central pyridine were pursued.