title: Synthesis of 5-(S)-HETE, 5-(S)-HEPE and (+)-zooxanthellactone: Three hydroxylated polyunsaturated fatty acid metabolites.
abstract: Short and stereoselective syntheses of the two hydroxylated polyunsaturated fatty acid metabolites, namely 5-(S)-HETE and 5-(S)-HEPE, are reported in 23% and 30% overall yields, respectively. In addition, synthesis of the polyunsaturated fatty acid natural product (+)-zooxanthellactone has been achieved in 19% overall yield. The three aforementioned compounds have been conveniently prepared in six steps, starting from the corresponding commercially available polyunsaturated fatty acids arachidonic acid, eicosapentaenoic acid and docosahexaenoic acid, respectively. All three hydroxylated polyunsaturated natural products were prepared using a biomimetic synthesis.
authors.affiliation: Department of Pharmaceutical Chemistry, School of Pharmacy, University of Oslo, P.O. Box 1068, Blindern, N-0316 Oslo, Norway.
authors.forename: Karoline Gangestad
authors.initials: KG
authors.lastname: Primdahl
authors.affiliation: Department of Chemistry, Biology and Food Science, Norwegian University of Life Sciences, P.O. Box 5003, N-1432, Ås, Norway.
authors.forename: Yngve
authors.initials: Y
authors.lastname: Stenstrøm
authors.affiliation: Department of Pharmaceutical Chemistry, School of Pharmacy, University of Oslo, P.O. Box 1068, Blindern, N-0316 Oslo, Norway; Department of Chemistry, Biology and Food Science, Norwegian University of Life Sciences, P.O. Box 5003, N-1432, Ås, Norway.
authors.forename: Trond Vidar
authors.initials: TV
authors.lastname: Hansen
authors.affiliation: Department of Pharmaceutical Chemistry, School of Pharmacy, University of Oslo, P.O. Box 1068, Blindern, N-0316 Oslo, Norway. Electronic address: anders.vik@farmasi.uio.no.
authors.forename: Anders
authors.initials: A
authors.lastname: Vik
mesh_terms: D066241:Carbon-13 Magnetic Resonance Spectroscopy; D015118:Eicosapentaenoic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D005231:Fatty Acids, Unsaturated / Q000138:chemical synthesis* / Q000378:metabolism*; D006893:Hydroxyeicosatetraenoic Acids / Q000138:chemical synthesis*; D006900:Hydroxylation; D007783:Lactones / Q000138:chemical synthesis*; D066244:Proton Magnetic Resonance Spectroscopy
chemical_list: D005231:Fatty Acids, Unsaturated; D006893:Hydroxyeicosatetraenoic Acids; D007783:Lactones; C022022:5-hydroxy-6,8,11,14-eicosatetraenoic acid; C058722:5-hydroxy-6,8,11,14,17-eicosapentaenoic acid; D015118:Eicosapentaenoic Acid
keywords: 5-(S)-HDHA; 5-(S)-HEPE; 5-(S)-HETE; Polyunsaturated fatty acids; Stereoselective reduction of enone