A stereoselective oxidation/double-Mannich approach to diverse alkaloid-like scaffolds

Sequential oxidative cleavage and double-Mannich reactions enable the stereoselective conversion of simple norbornene into complex alkaloid-like structures. The products undergo a wide range of derivatisation reactions, including a regioselective enol triflate formation cross-coupling sequences and highly efficient conversion to an unusual tricyclic-8,5,5 fused lactam. Overall the process represents a formal 1-atom aza-ring expansion with concomitant bridging annulation, making it of interest for the broader derivatisation of alkene feedstocks.