title: Synthesis of the CDE/FG ring models of prymnesins: reassignment of the relative configuration of the E/F ring juncture.
abstract: [structure: see text] Synthesis of two diastereomeric models (3a and 3b) corresponding to the CDE/FG ring of prymnesins, polycyclic ether toxins isolated from the red tide phytoflagellate Prymnesium parvum, is described. Comparison of the (1)H and (13)C NMR data for each compound with those reported for prymnesins suggests that the earlier stereochemical assignment of the E/F ring juncture needs to be revised.
authors.affiliation: Graduate School of Life Sciences, Tohoku University, Tsutsumidori-amamiya, Aoba-ku, Sendai 981-8555, Japan. masasaki@bios.tohoku.ac.jp
authors.forename: Makoto
authors.initials: M
authors.lastname: Sasaki
authors.forename: Makoto
authors.initials: M
authors.lastname: Ebine
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Takagi
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Takakura
authors.forename: Takeshi
authors.initials: T
authors.lastname: Shida
authors.forename: Masayuki
authors.initials: M
authors.lastname: Satake
authors.forename: Yasukatsu
authors.initials: Y
authors.lastname: Oshima
authors.forename: Tomoji
authors.initials: T
authors.lastname: Igarashi
authors.forename: Takeshi
authors.initials: T
authors.lastname: Yasumoto
mesh_terms: D004987:Ethers / Q000138:chemical synthesis* / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D008387:Marine Toxins / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D008968:Molecular Conformation; D061065:Polyketides; D011714:Pyrans / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D004987:Ethers; D006027:Glycosides; D006576:Heterocyclic Compounds, 4 or More Rings; D008387:Marine Toxins; D061065:Polyketides; D011714:Pyrans; C440216:prymnesin 1; C440215:prymnesin 2