PIDA-promoted intramolecular transannular aziridination to synthesize bridged azatricyclic amines related to methyllycaconitine

A synthetic strategy for the modeling construction of the A/E/F ring system of lycoctonine-type C19-diterpenoid alkaloids bearing a featuring oxygen functional group at C-7 has been successfully developed. The key steps involved a diastereoselective gold(I)-catalyzed annulation to form cis-fused cyclopentene and a PIDA-promoted intramolecular transannular aziridination followed by regioselective ring cleavage to give the azatricyclic amine.