Pyridone Annulation via Tandem Curtius Rearrangement/6π-Electrocyclization: Total Synthesis of (−)-Lyconadin C

摘要

A concise, enantioselective total synthesis of the Lycopodium alkaloid (−)-lyconadin C was achieved in 12 steps and high overall yield. Key features include construction of a luciduline congener through Mannich-type cyclization and a one-pot, tandem Curtius rearrangement/6π-electrocyclization to fashion the 2-pyridone system of lyconadin C.