Synthesis of tetrahydropyrroloiminoquinone alkaloids based on electrochemically generated hypervalent iodine oxidative cyclization.
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.
Inoue
Keisuke
K
Department of Chemistry, Faculty of Science and Technology, Keio University, Hiyoshi 3-14-1, Kohoku-ku, Yokohama 223-8522, Japan.
Ishikawa
Yuichi
Y
Nishiyama
Shigeru
S
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
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