title: Enantioselective total synthesis of eurylene, 14-deacetyl eurylene, and their 11-epimers: the relation between ionophoric nature and cytotoxicity.
abstract: [structure: see text] Enantioselective synthesis of eurylene, 14-deacetyl eurylene, and their 11-epimers was achieved. The characteristic structural feature of these compounds is two tetrahydrofuran (THF) rings substituted in different stereochemistry. The synthetic approach involves nonstereoselective THF ring formation to afford both segments from a common precursor. We also investigated their ionophoric nature and cytotoxicity. The complexation of these compounds with K(+) might be related to their cytotoxic activity.
authors.affiliation: Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima 770-8514, Japan.
authors.forename: Hideaki
authors.initials: H
authors.lastname: Hioki
authors.forename: Suzuyo
authors.initials: S
authors.lastname: Yoshio
authors.forename: Masatoshi
authors.initials: M
authors.lastname: Motosue
authors.forename: Yuka
authors.initials: Y
authors.lastname: Oshita
authors.forename: Yukari
authors.initials: Y
authors.lastname: Nakamura
authors.forename: Daisaku
authors.initials: D
authors.lastname: Mishima
authors.forename: Yoshiyasu
authors.initials: Y
authors.lastname: Fukuyama
authors.forename: Mitsuaki
authors.initials: M
authors.lastname: Kodama
authors.forename: Keisuke
authors.initials: K
authors.lastname: Ueda
authors.forename: Takashi
authors.initials: T
authors.lastname: Katsu
mesh_terms: D035701:Eurycoma; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology / Q000633:toxicity; D006801:Humans; D007476:Ionophores / Q000737:chemistry*; D007624:KB Cells; D015394:Molecular Structure; D024301:Plant Bark / Q000737:chemistry; D011188:Potassium / Q000737:chemistry; D014315:Triterpenes / Q000138:chemical synthesis*
chemical_list: C493364:14-deacetyl eurylene; D005663:Furans; D007476:Ionophores; D014315:Triterpenes; C493363:eurylene; C018674:tetrahydrofuran; D011188:Potassium