Divergent Total Syntheses of (−)-Lycopladine D, (+)-Fawcettidine, and (+)-Lycoposerramine Q

Enantioselective total syntheses of (+)-fawcettidine and (+)-lycoposerramine Q as well as the first total synthesis of (−)-lycopladine D from a common intermediate have been accomplished by a divergent path. The common intermediate was derived from a Hajos–Parrish-like diketone by a stereoselective Birch reduction and a Suzuki coupling. The synthesis of (−)-lycopladine D featured an allylic oxidation and a biomimetic aminoketalization while the route to (+)-fawcettidine and (+)-lycoposerramine Q highlighted an oxidative rearrangement.