title: Oxidative dearomatization/intramolecular Diels-Alder cycloaddition cascade for the syntheses of (±)-atisine and (±)-isoazitine.
abstract: A convergent and efficient formal synthesis of (±)-atisine has been accomplished. The synthetic strategy is to efficiently construct the bicyclo[2.2.2]octane ring moiety by an oxidative dearomatization/intramolecular Diels-Alder cycloaddition cascade. The first total synthesis of another atisine-type C(20)-diterpenoid alkaloid, (±)-isoazitine, has also been achieved employing the same strategy.
authors.affiliation: Department of Chemistry of Medicinal Natural Products, Sichuan University, No. 17, Duan 3, Renmin Nan Road, Chengdu, 610041.
authors.forename: Xiao-Yu
authors.initials: XY
authors.lastname: Liu
authors.forename: Hang
authors.initials: H
authors.lastname: Cheng
authors.forename: Xiao-Huan
authors.initials: XH
authors.lastname: Li
authors.forename: Qiao-Hong
authors.initials: QH
authors.lastname: Chen
authors.forename: Liang
authors.initials: L
authors.lastname: Xu
authors.forename: Feng-Peng
authors.initials: FP
authors.lastname: Wang
mesh_terms: D000470:Alkaloids / Q000737:chemistry*; D003500:Cyclization; D004224:Diterpenes / Q000737:chemistry*; D009795:Octanes / Q000737:chemistry; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D004224:Diterpenes; D009795:Octanes; C414609:isoazitine; C026728:octane