First total synthesis of 7(S),17(S)-Resolvin D5, a potent anti-inflammatory docosanoid |
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| Authors: | Ana R Rodríguez |
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| Institution: | Department of Cell Biology, University of Medicine and Dentistry of New Jersey, SOM, Stratford, NJ 08084, USA |
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| Abstract: | 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. |
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| Keywords: | Resolvins Hydrolytic kinetic resolution Palladium catalyst Takai reaction Lindlar reduction |
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