Stereoselective synthesis of maresin 1

Maresin 1 (1) is a potent anti-inflammatory and pro-resolving lipid mediator derived from docosahexaenoic acid. Total synthesis of maresin 1 (1) was achieved in 10 steps and in 7% overall yield. The Evans-Nagao aldol reaction between (2E,4E)-5-bromopenta-2,4-dienal (9) and different chiral auxiliaries was investigated. The synthetic material of 1 matched authentic material using HPLC-analysis. The reported synthesis is efficient and highly stereoselective, affording multi-mg quantities of this biologically interesting lipid mediator.