Stereoselective synthesis of the specialized pro-resolving and anti-inflammatory mediator resolvin E1

Abstract The n-3 polyunsaturated fatty acids eicosapentaenoic acid, docosahexaenoic acid and n-3 docosapentaenoic acid, act as substrates for the biosynthesis of specialized pro-resolving lipid mediators. Resolvin E1, produced from eicosapentaenoic acid, was the first specialized pro-resolving lipid mediator reported. This oxygenated polyunsaturated fatty acid displays a plethora of interesting biological activities, and has entered initial clinical trial development programs. The Evans-Nagao aldol reaction, a stereoselective alkyne reduction and a Z-selective Wittig reaction, were utilized for the stereocontrolled synthesis of resolvin E1 presented herein. In addition, results from HPLC analysis revealed that the synthetic material matched authentic resolvin E1.