Highly efficient terpenoid pheromone syntheses via regio-and stereocontrolled processing of allyllithiums generated by reductive lithiation of allyl phenyl thioethers

Article abstract of DOI:10.1016/S0040-4020(01)80712-2

Previous work had shown that reducuve lithiation of allyl phenyl thioethers, followed by transmetallation, produces allylmetallics which react selectively with carbonyl compounds at the most or least substituted terminus; the latter results in mainly cis olefin. This technology allows extremely efficient syntheses of racemic versions of lavandulol (two-pot, 70% yield), the Comstock mealy bug pheromone (one-pot, 45% yield) and the California red scale pheromone (4-steps, 23% yield).