title: Unexpected Diels-Alder/carbonyl-ene cascade toward the biomimetic synthesis of chloropupukeananin.
abstract: The biomimetic synthesis of the advanced model compound of chloropupukeananin has been achieved. The present synthesis features an unexpected enantiomer-differentiating Diels-Alder/carbonyl-ene cascade under high-pressure conditions and a base-promoted migration of the salicyl group.
authors.affiliation: Faculty of Pharmaceutical Sciences, Tokyo University of Science, 2641 Yamazaki, Noda-shi, Chiba 278-8510, Japan.
authors.forename: Takahiro
authors.initials: T
authors.lastname: Suzuki
authors.forename: Yuria
authors.initials: Y
authors.lastname: Miyajima
authors.forename: Kaname
authors.initials: K
authors.lastname: Suzuki
authors.forename: Kanako
authors.initials: K
authors.lastname: Iwakiri
authors.forename: Masaki
authors.initials: M
authors.lastname: Koshimizu
authors.forename: Go
authors.initials: G
authors.lastname: Hirai
authors.forename: Mikiko
authors.initials: M
authors.lastname: Sodeoka
authors.forename: Susumu
authors.initials: S
authors.lastname: Kobayashi
mesh_terms: D032701:Biomimetics; D008958:Models, Molecular; D015394:Molecular Structure; D012459:Salicylates / Q000737:chemistry; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D012459:Salicylates; D012717:Sesquiterpenes; C529542:chloropupukeananin