Synthesis of the methyl ester of 17(R/S)-Me-RvD5(n-3 DPA) and relief of postoperative pain in male mice

The synthesis and biological evaluation of 17(R/S)-Me-RvD5(n-3 DPA), an analog of the specialized pro-resolving mediators RvD5 and RvD5(n-3 DPA), are presented. The synthesis was successfully accomplished utilizing Midland Alpine borane reduction, Sonogashira cross-coupling and a one-pot hydrozirconation/iodination protocol. In vivo evaluation of RvD5, RvD5(n-3 DPA) and 17(R/S)-Me-RvD5(n-3 DPA) in a mouse model of fracture revealed that all three compounds inhibited postoperative pain in male mice, but not in female mice.