Total synthesis of the potent anti-inflammatory lipid mediator Protectin D1 |
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Authors: | Ana R Rodriguez Bernd W Spur |
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Institution: | Department of Cell Biology, Rowan University-SOM, Stratford, NJ 08084, USA |
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Abstract: | The total synthesis of the potent anti-inflammatory lipid mediator Protectin D1 derived from docosahexaenoic acid, has been achieved. The chiral hydroxy-groups at C10 and C17 were obtained via a chiral pool strategy from (4R)-4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane and 3,4-O-isopropylidene-2-deoxy-d-ribose, respectively. Wittig reactions, Takai olefination, Pd0/CuI Sonogashira coupling, and Zn(Cu/Ag) reduction completed the total synthesis of Protectin D1. |
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Keywords: | Protectin D1/Neuroprotectin D1 Total synthesis Inflammation resolution Wittig reaction Takai olefination Sonogashira coupling |
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