title: Biomimetic epoxide-opening cascades of oxasqualenoids triggered by hydrolysis of the terminal epoxide.
abstract: The biomimetic epoxide-opening cascades from squalene polyepoxides 4-6 to triterpene polyethers (oxasqualenoids) teurilene (1), glabrescol (2), and omaezakianol (3), respectively, were reproduced in a single event by chemical reaction. These cascades proceeded through the 5-exo tandem cyclization triggered by Brønsted acid-catalyzed hydrolysis of the terminal epoxide, mimicking the direct hydrolysis mechanism of epoxide hydrolases.
authors.affiliation: Department of Chemistry, Graduate School of Science, Osaka City University , Sumiyoshi-ku, Osaka 558-8585, Japan.
authors.forename: Yoshiki
authors.initials: Y
authors.lastname: Morimoto
authors.forename: Eriko
authors.initials: E
authors.lastname: Takeuchi
authors.forename: Hitomi
authors.initials: H
authors.lastname: Kambara
authors.forename: Takeshi
authors.initials: T
authors.lastname: Kodama
authors.forename: Yoshimitsu
authors.initials: Y
authors.lastname: Tachi
authors.forename: Keisuke
authors.initials: K
authors.lastname: Nishikawa
mesh_terms: D032701:Biomimetics; D004851:Epoxide Hydrolases / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry*; D005663:Furans / Q000737:chemistry*; D006868:Hydrolysis; D015394:Molecular Structure; D013185:Squalene / Q000031:analogs & derivatives* / Q000737:chemistry*; D013237:Stereoisomerism; D014315:Triterpenes / Q000737:chemistry*
chemical_list: D004852:Epoxy Compounds; D005663:Furans; D014315:Triterpenes; C540153:omaezakianol; C463400:teurilene; C116803:glabrescol; D013185:Squalene; D004851:Epoxide Hydrolases