Total synthesis of the macrophage derived anti-inflammatory lipid mediator Maresin 1

The total synthesis of Maresin 1, an endogenous macrophage pro-resolving lipid mediator derived from docosahexaenoic acid, has been achieved. The chiral hydroxy-group at C7 was obtained via a Jacobsen hydrolytic kinetic resolution of a terminal epoxide whereas the center at C14 arises from a chiral pool strategy starting from 2-deoxy-d-ribose. Pd0/CuI Sonogashira coupling of the two key fragments and Zn(Cu/Ag) reduction completed the total synthesis of Maresin 1.