First total synthesis of 7(S),17(S)-Resolvin D5, a potent anti-inflammatory docosanoid

The first total synthesis of 7(S),17(S)-Resolvin D5, a lipid mediator derived from docosahexaenoic acid, has been achieved. The chiral centers were generated via a Co-salen hydrolytic kinetic resolution of a terminal epoxide with >99% ee. Key steps include Takai olefination, Pd0/CuI coupling and simultaneous deprotection and ester cleavage with lipase from Candida rugosa.