Synthesis of 4-methyldienoates using a vinylogous Horner-Wadsworth-Emmons reagent. Application to the synthesis of trichostatic acid.
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.
Markiewicz
John T
JT
Department of Chemistry and Biochemistry, Walther Cancer Research Center, University of Notre Dame, 251 Nieuwland Science Hall, Notre Dame, Indiana 46556, USA.
Schauer
Douglas J
DJ
Löfstedt
Joakim
J
Corden
Steven J
SJ
Wiest
Olaf
O
Helquist
Paul
P
D020650:Combinatorial Chemistry Techniques; D005231:Fatty Acids, Unsaturated / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D005231:Fatty Acids, Unsaturated; D009943:Organophosphorus Compounds; C066131:trichostatic acid