title: Enantioselective Synthesis of (-)-Dysiherbaine.
abstract: Dysiherbaine, a natural product isolated from the Marine sponge Dysidea herbacea, has been shown to be a selective agonist of non-NMDA type glutamate receptors, kainate receptors. An enantioselective synthesis of dysiherbaine is reported. Metathesis of the diene followed by conversion of the resulting alkene to the amino alcohol and addition of the amino acid provides the natural product. This synthesis differs from previous approaches to the molecule in that the functionality on the tetrahydropyran ring is installed late in the route.
authors.affiliation: Department of Chemistry, University of Houston, Houston, Texas 77204, United States.
authors.forename: Ha
authors.initials: H
authors.lastname: Do
authors.affiliation: Department of Chemistry, University of Houston, Houston, Texas 77204, United States.
authors.forename: Chang Won
authors.initials: CW
authors.lastname: Kang
authors.affiliation: Department of Chemistry, University of Houston, Houston, Texas 77204, United States.
authors.forename: Joon Hyung
authors.initials: JH
authors.lastname: Cho
authors.affiliation: Department of Chemistry, University of Houston, Houston, Texas 77204, United States.
authors.forename: Scott R
authors.initials: SR
authors.lastname: Gilbertson
mesh_terms: D000409:Alanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000475:Alkenes / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry; D000818:Animals; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D008386:Marine Biology; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry*; D017470:Receptors, Glutamate / Q000187:drug effects; D018092:Kainic Acid Receptors / Q000187:drug effects*; D013237:Stereoisomerism
chemical_list: D000409:Alanine; D000475:Alkenes; D000596:Amino Acids; D001688:Biological Products; D019086:Bridged Bicyclo Compounds, Heterocyclic; D017470:Receptors, Glutamate; D018092:Kainic Acid Receptors; C121741:dysiherbaine