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Synthesis of 4-Methyldienoates Using a Vinylogous Horner−Wadsworth−Emmons Reagent. Application to the Synthesis of Trichostatic Acid

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journal contribution
posted on 19.03.2010, 00:00 by John T. Markiewicz, Douglas J. Schauer, Joakim Löfstedt, Steven J. Corden, Olaf Wiest, Paul Helquist
The utility of the unsaturated phosphonate 1 as a vinylogous Horner−Wadsworth−Emmons reagent was explored in reactions with aldehydes affording 4-methyldienoate esters. Factors that affect E/Z selectivity were studied. A simplified synthesis of trichostatic acid 3 was accomplished to demonstrate utility of this reagent.