Tetrahedron

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

DW McCullough, M Bhupathy, E Piccolino, T Cohen

Index: McCullough, Dennis W.; Bhupathy; Piccolino, Elvio; Cohen, Theodore Tetrahedron, 1991 , vol. 47, # 47 p. 9727 - 9736

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Citation Number: 31

Abstract

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 ...