4.7 Article

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

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 75, Issue 6, Pages 2061-2064

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo902422y

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Funding

  1. Walther Cancer Institute, Circagen
  2. Ara Parseghian Medical Research Foundation

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The utility of the unsaturated phosphonate 1 its it 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.

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