title: Tandem C-H oxidation/cyclization/rearrangement and its application to asymmetric syntheses of (-)-brussonol and (-)-przewalskine E.
abstract: Natural products are a vital source of lead compounds in drug discovery. Development of efficient tandem reactions to build useful compounds and apply them to the synthesis of natural products is not only a significant challenge but also an important goal for chemists. Here we describe a tandem C-H oxidation/cyclization/rearrangement of isochroman-derived allylic silylethers, promoted by DDQ and InCl3. This method allows the efficient construction of tricyclic benzoxa[3.2.1]octanes with a wide substrate scope. We employ this tandem reaction to achieve the asymmetric total syntheses of (-)-brussonol and (-)-przewalskine E.
authors.affiliation: State Key Laboratory of Applied Organic Chemistry &College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. China.
authors.forename: Zhi-Wei
authors.initials: ZW
authors.lastname: Jiao
authors.affiliation: 1] State Key Laboratory of Applied Organic Chemistry &College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. China [2] Collaborative Innovation Center of Chemical Science and Engineering, Tianjin 300071, P. R. China.
authors.forename: Yong-Qiang
authors.initials: YQ
authors.lastname: Tu
authors.affiliation: State Key Laboratory of Applied Organic Chemistry &College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. China.
authors.forename: Qing
authors.initials: Q
authors.lastname: Zhang
authors.affiliation: State Key Laboratory of Applied Organic Chemistry &College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. China.
authors.forename: Wen-Xing
authors.initials: WX
authors.lastname: Liu
authors.affiliation: State Key Laboratory of Applied Organic Chemistry &College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. China.
authors.forename: Shu-Yu
authors.initials: SY
authors.lastname: Zhang
authors.affiliation: State Key Laboratory of Applied Organic Chemistry &College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. China.
authors.forename: Shao-Hua
authors.initials: SH
authors.lastname: Wang
authors.affiliation: State Key Laboratory of Applied Organic Chemistry &College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. China.
authors.forename: Fu-Min
authors.initials: FM
authors.lastname: Zhang
authors.affiliation: State Key Laboratory of Applied Organic Chemistry &College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. China.
authors.forename: Sen
authors.initials: S
authors.lastname: Jiang
mesh_terms: D016227:Benzoquinones / Q000737:chemistry*; D004224:Diterpenes / Q000138:chemical synthesis*; D007204:Indium / Q000737:chemistry*
chemical_list: D016227:Benzoquinones; D004224:Diterpenes; C502780:brussonol; C000606765:przewalskine E; D007204:Indium; C000928:dichlorodicyanobenzoquinone; C020758:indium trichloride