title: Synthesis of tetrahydropyrroloiminoquinone alkaloids based on electrochemically generated hypervalent iodine oxidative cyclization.
abstract: An approach to the synthesis of the tetrahydropyrroloiminoquinone alkaloids has been developed and applied to the preparation of N-1-beta-D-ribofuranosyltetrahydropyrroloiminoquinones. The strategy utilizes oxidative cyclization of aryl-methoxyamides by hypervalent iodine to construct the quinoline framework shared by members of this alkaloid family. The hypervalent iodine oxidant is generated in situ by anodic oxidation of iodobenzene.
authors.affiliation: Department of Chemistry, Faculty of Science and Technology, Keio University, Hiyoshi 3-14-1, Kohoku-ku, Yokohama 223-8522, Japan.
authors.forename: Keisuke
authors.initials: K
authors.lastname: Inoue
authors.forename: Yuichi
authors.initials: Y
authors.lastname: Ishikawa
authors.forename: Shigeru
authors.initials: S
authors.lastname: Nishiyama
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D000818:Animals; D002384:Catalysis; D019008:Drug Resistance, Neoplasm / Q000187:drug effects; D004354:Drug Screening Assays, Antitumor; D005260:Female; D006801:Humans; D007462:Iodobenzenes / Q000737:chemistry; D007624:KB Cells; D008386:Marine Biology; D051379:Mice; D015394:Molecular Structure; D009005:Monosaccharides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D010084:Oxidation-Reduction; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D047608:Pyrroloiminoquinones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism; D059005:Topoisomerase II Inhibitors
chemical_list: D000470:Alkaloids; D007462:Iodobenzenes; D009005:Monosaccharides; C547266:N-1-beta-D-ribofuranosyldamirone C; C547265:N-1-beta-D-ribofuranosylmakaluvamine I; D011758:Pyrroles; D047608:Pyrroloiminoquinones; D059005:Topoisomerase II Inhibitors; C031905:iodobenzene