title: Stereocontrolled total synthesis of the potent anti-inflammatory and pro-resolving lipid mediator resolvin D3 and its aspirin-triggered 17R-epimer.
abstract: The first total synthesis of stereochemically pure resolvin D3 and aspirin-triggered resolvin D3 is reported. These enzymatic metabolites of docosahexaenoic acid (DHA) have potent anti-inflammatory and pro-resolving actions. The convergent synthetic strategy is based on enantiomerically pure starting materials, and it is highly stereocontrolled.
authors.affiliation: Department of Chemistry and Loker Hydrocarbon Research Institute, University of Southern California, Los Angeles, California 90089, USA.
authors.forename: Jeremy W
authors.initials: JW
authors.lastname: Winkler
authors.forename: Jasim
authors.initials: J
authors.lastname: Uddin
authors.forename: Charles N
authors.initials: CN
authors.lastname: Serhan
authors.forename: Nicos A
authors.initials: NA
authors.lastname: Petasis
mesh_terms: D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001241:Aspirin / Q000494:pharmacology*; D005231:Fatty Acids, Unsaturated / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D018836:Inflammation Mediators / Q000502:physiology; D050356:Lipid Metabolism; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000894:Anti-Inflammatory Agents, Non-Steroidal; D005231:Fatty Acids, Unsaturated; D018836:Inflammation Mediators; C583088:resolvin D3; D001241:Aspirin