The total synthesis of Protectin DX, a proresolving mediator derived biosynthetically from docosahexaenoic acid, has been achieved in 25 steps with a 1.3% overall yield. The highly stereocontrolled synthetic strategy utilizes the chiral pool which provides the 10(S) and 17(S) hydroxyl groups. The synthesis also included <i>Z</i> and <i>E</i> selective Wittig reactions, partial reduction using Zn(Cu/Ag), Takai olefination, and Sonogashira coupling.

Total synthesis of protectin DX, a potent proresolving lipid mediator

256th National Meeting (2018)

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