title: Stereoselective synthesis of (all-Z)-hentriaconta-3,6,9,12,15,19,22,25,28-nonaene.
abstract: Several microorganisms produce small quantities of polyunsaturated hydrocarbons and such natural products are of interest. Starting from the ethyl ester of eicosapentaenoic acid, the total synthesis of the natural product (all-Z)-hentriaconta-3,6,9,12,15,19,22,25,28-nonaene has been achieved in eight steps and 15% overall yield. The synthesis is based on a stereoselective Wittig reaction and confirms the all-Z-configuration of the nine double bonds in this highly unsaturated natural product.
authors: Department of Chemistry, Biology and Food Science, Norwegian University of Life Sciences, PO Box 5003, N-1432, Ås, Norway. yngve.stenstrom@nmbu.no.
authors: Liudmila
authors: L
authors: Filippova
authors: Ida
authors: I
authors: Aarum
authors: Martine
authors: M
authors: Ringdal
authors: Martin Kirkhus
authors: MK
authors: Dahl
authors: Trond Vidar
authors: TV
authors: Hansen
authors: Yngve
authors: Y
authors: Stenstrøm
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D015195:Drug Design; D015118:Eicosapentaenoic Acid / Q000031:analogs & derivatives* / Q000737:chemistry; D004952:Esters / Q000737:chemistry; D005231:Fatty Acids, Unsaturated / Q000737:chemistry; D006838:Hydrocarbons / Q000737:chemistry*; D050356:Lipid Metabolism; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D001688:Biological Products; D004952:Esters; D005231:Fatty Acids, Unsaturated; D006838:Hydrocarbons; C000599522:hentriaconta-3,6,9,12,15,19,22,25,28-nonene; D015118:Eicosapentaenoic Acid