- Highly efficient terpenoid pheromone syntheses via regio-and stereocontrolled processing of allyllithiums generated by reductive lithiation of allyl phenyl thioethers
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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).
- McCullough, Dennis W.,Bhupathy,Piccolino, Elvio,Cohen, Theodore
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p. 9727 - 9736
(2007/10/02)
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