Parinaric acid is a widely used fluorescent probe of biological systems. The ail-trans isomer (9 (E), ll (E), l3-(E), 15 (E)-octadecatetraenoic acid) specifically deuteriated at all vinyl positions was prepared by using the Wittig reaction to couple a diene phosphorane with an a, P-unsaturated aldehydeester. The preparation of each component included the stereoselective reduction of a substituted propynoic ester with lithium aluminum deuteride ...
