139115-22-3Relevant articles and documents
Highly efficient terpenoid pheromone syntheses via regio-and stereocontrolled processing of allyllithiums generated by reductive lithiation of allyl phenyl thioethers
McCullough, Dennis W.,Bhupathy,Piccolino, Elvio,Cohen, Theodore
, p. 9727 - 9736 (1991)
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).
