Total synthesis of (-)-goniomitine

The total synthesis of (-)-goniomitine has been accomplished in 11 steps starting from commercially available diethyl l-malate. The synthesis features a chiral pool approach to prepare the chiral C-9 unit containing a quaternary carbon center, an Ir-catalyzed C-H borylation to synthesize the 2-indoleboronic acid pinacol ester, and a Suzuki reaction to couple together the two key intermediates. Notably, the high degree of convergence of this strategy makes it particularly amenable to the total synthesis of other aspidosperma family natural products.