Synthetic anthracyclines: regiospecific total synthesis of a D-ring indole analogue of daunomycin.
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).
Kita
Y
Y
Faculty of Pharmaceutical Sciences, Osaka University, Japan.
Kirihara
M
M
Sasho
M
M
Fujii
Y
Y
Sekihachi
J
J
Okunaka
R
R
Tamura
Y
Y
Shimooka
K
K
D000818:Animals; D055598:Chemical Phenomena; D002621:Chemistry; D003630:Daunorubicin / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D051379:Mice; D014407:Tumor Cells, Cultured / Q000187:drug effects
D003630:Daunorubicin