Construction of vicinal quaternary carbon atoms by Ireland ester Claisen rearrangement: total synthesis of (±)-herbertenolide, (±)-herberteneacetal, (±)-herbertene-1,14-diol and (±)-herbertene-1,15-diol

Efficient total syntheses of the herbertane sesquiterpene title compounds have been accomplished employing an Ireland ester Claisen rearrangement and ring-closing metathesis reaction sequence based strategy for the construction of two stereogenic vicinal quaternary carbon atoms on a cyclopentane.