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.