Convergent synthesis of ( R, R)-6,12-dimethylpentadecan-2-one, the female sex pheromone of the banded cucumber beetle by iron mediated chirality transfer

Abstract

The highly convergent synthesis of ( R, R)-6,12-dimethylpentadecan-2-one [( R, R)- 1], the bioactive form of the sex pheromone produced by female adults of the banded cucumber beetle Diabrotica balteata LeConte, in high enantio- and diastereomeric purity ( ee ≥ 99%, de ≥ 98%) and good overall yield (13 steps, 39%) is described. The stereogenic centres were generated by nucleophilic addition of allyltrimethylsilane to an enantiopure planar chiral (π-allyl)-tetracarbonyliron(1+)-complex.