Synthesis Of (+/-)-Aureol By Bioinspired Rearrangements

A bioinspired and sustainable procedure for the straightforward synthesis of (+/-)-aureol has been achieved in eight steps (14% overall yield) from epoxyfarnesol. The key steps are the titanocene(III)-catalyzed radical cascade cyclization of an epoxyfarnesol derivative and a biosynthetically inspired sequence of 1,2-hydride and methyl shifts.