Approaches to the synthesis of the galbulimima alkaloid himandrine

The hexacyclic skeleton of himandrine (2), which is present in 15 of the more complex alkaloids obtained from the bark of the tropical rain forest tree Galbulimima belgraveana has been prepared by means of a 19-step synthesis beginning with the known [3.2.1]-benzobicyclooctene intermediate 9. An alternative approach is also described, thus far culminating in 34. Key transformations include DielsAlder cycloadditions, ring contractions, a Curtius rearrangement, a Birch reduction, an intramolecular nucleophilic amination, and a palladium-mediated alkene amination.