title: The absolute configuration of ecklonialactones A, B, and E, novel oxylipins from brown algae of the genera Ecklonia and Egregia.
abstract: Ecklonialactones A, B, and E, previously isolated from the brown alga Ecklonia stolonifera, have been isolated from the Oregon phaeophyte Egregia menziesii. The structure and relative stereochemistry of ecklonialactone E were independently determined by various nmr techniques. The absolute stereochemistry of ecklonialactone A was deduced by cd analysis of a dibenzoate derivative, which indicated it possessed a 11S, 12R, 13S, 15R, 16S stereochemistry. Similar 1H- and 13C-nmr data and optical rotations for all of the ecklonialactones indicate that B and E have the same stereochemistry as A at comparable stereocenters.
authors.affiliation: College of Pharmacy, Oregon State University, Corvallis 97331.
authors.forename: J S
authors.initials: JS
authors.lastname: Todd
authors.forename: P J
authors.initials: PJ
authors.lastname: Proteau
authors.forename: W H
authors.initials: WH
authors.lastname: Gerwick
mesh_terms: D001643:Bridged Bicyclo Compounds / Q000737:chemistry* / Q000302:isolation & purification; D018360:Crystallography, X-Ray; D007783:Lactones / Q000737:chemistry* / Q000302:isolation & purification; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D000459:Phaeophyceae / Q000737:chemistry*
chemical_list: D001643:Bridged Bicyclo Compounds; D007783:Lactones; C086784:ecklonialactone A; C086785:ecklonialactone B; C086786:ecklonialactone E