Synthetic Anthracyclines : Regiospecific Total Synthesis of a D-Ring Indole Analogue of Daunomycin

The 4-methoxy-5-methylpyrano[3, 4, -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-ehylenedioxy-5, 6, 7, 8-tetrahydro-1, 4-naphtoquinone (11) to give the tetrahydronapht...

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Published inChemical & pharmaceutical bulletin Vol. 38; no. 3; pp. 585 - 589
Main Authors KITA, Yasuyuki, SASHO, Manabu, SEKIHACHI, Jun-ichi, SHIMOOKA, Kino-o, FUJII, Yuji, OKUNAKA, Ryuichi, TAMURA, Yasumitsu, KIRIHARA, Masayuki
Format Journal Article
LanguageEnglish
Published Japan The Pharmaceutical Society of Japan 01.03.1990
公益社団法人日本薬学会
Subjects
Animals
antitumor agent
Chemical Phenomena
Chemistry
cycloaddition
D-ring indole analogue
daunomycin analogue
Daunorubicin - analogs & derivatives
Daunorubicin - chemical synthesis
heteroanthracycline
Mice
Tumor Cells, Cultured - drug effects
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ISSN0009-2363
1347-5223
DOI10.1248/cpb.38.585

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Summary:The 4-methoxy-5-methylpyrano[3, 4, -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-ehylenedioxy-5, 6, 7, 8-tetrahydro-1, 4-naphtoquinone (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).
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ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.38.585