ARS | Publication request: Progress on the Synthesis of Hydroxy Phosphonates Vis Lesquerella Oil

Submitted to: Great Lakes Regional American Chemical Society Symposium
Publication Acceptance Date: September 13, 2004
Publication Date: October 20, 2004
Citation: Deppe, A.B., Cermak, S.C., Isbell, T., Cermak, D.M. 2004. Progress On The Synthesis Of Hydroxy Phosphonates Vis Lesquerella Oil. Great Lakes Regional American Chemical Society Symposium.

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 synthesis of these compounds will be presented.