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Synthesis 1991; 1991(12): 1235-1244
DOI: 10.1055/s-1991-28426
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A Novel Palladium-Catalyzed Deoxygenation of Enediols to 1,3-Dienes

Barry M. Trost* , Gerald B. Tometzki
  • *Departments of Chemistry, University of Wisconsin-Madison, Madison, WI 53706, USA, and Stanford University, Stanford, CA 94305-5080, USA
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Publikationsdatum:
29. April 2002 (online)

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Hydroxylative Knoevenagel condensation of aldehydes followed by reduction provides a simple entry to 1,4-enediols. Subjecting the dicarbonate to a palladium(0) catalyst in the presence of triisopropyl phosphite achieves a mild vinylogous deoxygenation to (E)-1,3-dienes. Stereocontrolled synthesis of the sex pheromone of the red bollworm moth, (E)-9,11-dodecadienyl acetate, and a formal synthesis of the cotton boll weevil antifeedant, α-eleostearic acid, demonstrate the utility of this new methodology.