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

AR Rodriguez, BW Spur - Tetrahedron Letters, 2012 - Elsevier
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.