Bioinspired Total Synthesis of (±)-Yezo’otogirin C

The first and protective group-free total synthesis of (±)-yezo’otogirin C has been achieved from 3-methyl-4-prenylcyclohex-2-enone in eight steps with 23% overall yield. The tricyclic core of (±)-yezo’otogirin C was established via a bioinspired oxidative cascade cyclization strategy using Mn­(II)/Mn­(III) and O2, followed by reduction of the peroxy-bridged intermediate using thiourea in refluxing methanol.