Total Synthesis of (-)-Geissoschizol through Ir-Catalyzed Allylic Amidation as the Key Step.

The iridium-catalyzed, Zn(OTf)2 promoted asymmetric allylic amidation of a secondary alcohol derived from tryptamine has been utilized to forge a tetrahydro-β-carboline. Based on this key step, a novel, facile, and enantioselective total synthesis of (-)-geissoschizol was achieved in 10 steps.