Submitted to: Journal of the American Oil Chemists' Society
Publication Type: Abstract Only
Publication Acceptance Date: May 7, 2003
Publication Date: N/A
Technical Abstract: Lesquerella fendleri is developing oilseed crop currently grown in the Southwestern U.S. The oil is very attractive due to high levels of hydroxy fatty acids 53%, 14-hydroxy-cis-11-eicosenoic acid (lesquerolic acid). A lesquerolic acid derivative underwent a Pudovic reaction to produce a new chiral, nonracemic dihydroxy phosphonate, as well as a Horner Wadsworth Emmons (HWE) condensation to produce a chiral, nonracemic hydroxy vinyl phosphonate. Previously synthesized phosphonates, when converted to their corresponding phosphonic acids, have shown important biological activity as enzyme inhibitors. It has also been demonstrated that the absolute configuration of these compounds has a direct impact on their biological efficacy. The results of the synthesis of these compounds will be discussed.