title: Divergent total synthesis of taiwaniaquinones A and F and taiwaniaquinols B and D.
abstract: A divergent approach was developed toward the total synthesis of taiwaniaquinoids. An advanced intermediate 5a with trans A/B ring junction was concisely assembled by employing a Bi(OTf)3-catalyzed cationic cyclization and a Wolff-type ring contraction as key steps. This common intermediate was readily converted to racemic taiwaniaquinones A and F and taiwaniaquinols B and D, respectively.
authors.affiliation: State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.
authors.forename: Jun
authors.initials: J
authors.lastname: Deng
authors.forename: Ruofan
authors.initials: R
authors.lastname: Li
authors.forename: Yijie
authors.initials: Y
authors.lastname: Luo
authors.forename: Jian
authors.initials: J
authors.lastname: Li
authors.forename: Shupeng
authors.initials: S
authors.lastname: Zhou
authors.forename: Yongjian
authors.initials: Y
authors.lastname: Li
authors.forename: Jingyu
authors.initials: J
authors.lastname: Hu
authors.forename: Ang
authors.initials: A
authors.lastname: Li
mesh_terms: D002384:Catalysis; D003500:Cyclization; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011809:Quinones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D004224:Diterpenes; D011809:Quinones; C505702:taiwaniaquinol B; C582946:taiwaniaquinol D; C556365:taiwaniaquinone A; C556366:taiwaniaquinone F