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.
Department of Chemistry and Biochemistry, Walther Cancer Research Center, University of Notre Dame, 251 Nieuwland Science Hall, Notre Dame, Indiana 46556, USA.
John T
JT
Markiewicz
Douglas J
DJ
Schauer
Joakim
J
Löfstedt
Steven J
SJ
Corden
Olaf
O
Wiest
Paul
P
Helquist
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