Total synthesis of (±)-simonsol C using dearomatization as key reaction under acidic conditions

The total synthesis of (±)-simonsol C was accomplished using a dearomatization under acidic conditions as key step to construct an aryl-containing quaternary center. The 6/5/6 benzofuran unit was formed through reductive elimination with Zn/AcOH and a spontaneous oxy-Michael addition. This synthesis consists of 8 steps and achieves an overall yield of 13%, making it the shortest known route.