title: Stereoselective synthesis of protectin D1: a potent anti-inflammatory and proresolving lipid mediator.
abstract: A convergent stereoselective synthesis of the potent anti-inflammatory, proresolving and neuroprotective lipid mediator protectin D1 (2) has been achieved in 15% yield over eight steps. The key features were a stereocontrolled Evans-aldol reaction with Nagao's chiral auxiliary and a highly selective Lindlar reduction of internal alkyne 23, allowing the sensitive conjugated E,E,Z-triene to be introduced late in the preparation of 2. The UV and LC/MS-MS data of synthetic protectin D1 (2) matched those obtained from endogenously produced material.
authors.affiliation: School of Pharmacy, Department of Pharmaceutical Chemistry, University of Oslo, PO Box 1068 Blindern, N-0316 Oslo, Norway. t.v.hansen@farmasi.uio.no.
authors.forename: M
authors.initials: M
authors.lastname: Aursnes
authors.forename: J E
authors.initials: JE
authors.lastname: Tungen
authors.forename: A
authors.initials: A
authors.lastname: Vik
authors.forename: J
authors.initials: J
authors.lastname: Dalli
authors.forename: T V
authors.initials: TV
authors.lastname: Hansen
mesh_terms: D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D004281:Docosahexaenoic Acids / Q000096:biosynthesis / Q000138:chemical synthesis* / Q000737:chemistry; D008055:Lipids / Q000737:chemistry*; D051379:Mice; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000894:Anti-Inflammatory Agents, Non-Steroidal; D008055:Lipids; C487679:protectin D1; D004281:Docosahexaenoic Acids