Convergent Synthesis of (R,R)-6,12-Dimethylpentadecan-2-one, the Female Sex Pheromone of the Banded Cucumber Beetle by Iron Mediated Chirality Transfer

Article abstract of DOI:10.1016/0040-4020(95)00282-D

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 >/= 99percent, de >/= 98percent) and good overall yield (13 steps, 39percent) is described.The stereogenic centres were generated by nucleophilic addition of allyltrimethylsilane to an enantiopure planar chiral (?-allyl)-tetracarbonyliron(1+)-complex.