Tetrahedron p. 2469 - 2474 (1986)
Update date:2022-08-04
Topics: Synthesis Pheromones
Julia, Marc
Stacino, Jean-Pierre
The title compounds Z,8-dodecen-1yl acetate, Z,9-dodecen-1yl acetate and Z,9-tetradecen-1yl-acetate have been synthesized in three efficient steps: the reaction mixture from metalated ω-hydroxy sulfones and appropriate aldehydes was quenched with acetic anhydride yielding a diastereoisomeric mixture of β-acetoxy sulfones.Convergent elimination with powdered sodium hydroxide led to the E vinylic sulfone.Stereospecific hydrogenolysis of the sulfonyl group was carried out with sodium dithionite leading to the unsaturated alcohol (> 99percent Z).
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