title: Synthetic anthracyclines: regiospecific total synthesis of a D-ring indole analogue of daunomycin.
abstract: The 4-methoxy-5-methylpyrano[4,3-b]indole-1,3(4H,5H)-dione (9), prepared from methyl 3-methoxycarbonyl-1-methylindol-2-yl acetate (6), underwent a strong base-induced cycloaddition reaction with 2-chloro-6,6-ethylenedioxy-5,6,7,8-tetrahydro-1,4-naphthoquinone (11) to give the tetrahydronaphtho[2,3-b]carbazole-7,12-dione (10), regioselectively. The cycloadduct (10) was successfully converted to a D-ring indole analogue of daunomycin (1a).
authors.affiliation: Faculty of Pharmaceutical Sciences, Osaka University, Japan.
authors.forename: Y
authors.initials: Y
authors.lastname: Kita
authors.forename: M
authors.initials: M
authors.lastname: Kirihara
authors.forename: M
authors.initials: M
authors.lastname: Sasho
authors.forename: Y
authors.initials: Y
authors.lastname: Fujii
authors.forename: J
authors.initials: J
authors.lastname: Sekihachi
authors.forename: R
authors.initials: R
authors.lastname: Okunaka
authors.forename: Y
authors.initials: Y
authors.lastname: Tamura
authors.forename: K
authors.initials: K
authors.lastname: Shimooka
mesh_terms: D000818:Animals; D055598:Chemical Phenomena; D002621:Chemistry; D003630:Daunorubicin / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D051379:Mice; D014407:Tumor Cells, Cultured / Q000187:drug effects
chemical_list: D003630:Daunorubicin