SYNTHESIS OF THE NATURALLY-OCCURRING INDOLEQUINONE BE-10988, AN INHIBITOR OF TOPOISOMERASE-2

被引：31
作者：
MOODY, CJ
SWANN, E
机构：
[1] Department of Chemistry, University of Loughborough
来源：
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1993年 / 21期
关键词：
D O I：
10.1039/p19930002561
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A short synthesis (28% overall yield) of the naturally occurring indolequinone BE 10988 1 is described. The synthesis starts from 4-benzyloxy-5-methoxyindole and involves, as key steps, the use of chlorosulfonyl isocyanate to introduce the amide side-chain into the indole 3-position, followed by thioamide formation and construction of the thiazole ring using a Hantzsch reaction.
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页码：2561 / 2565
页数：5
相关论文
共 24 条
  • [1] NONSTEROIDAL ANTIINFLAMMATORY AGENTS .2. SYNTHESIS AND BIOLOGICAL-ACTIVITY OF 2-CHLOROINDOLECARBOXYLIC ACIDS
    ANDREANI, A
    BONAZZI, D
    RAMBALDI, M
    GUARNIERI, A
    ANDREANI, F
    STROCCHI, P
    MONTANARO, N
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1977, 20 (10) : 1344 - 1346
  • [2] THE SYNTHESIS OF 7-ALKOXYINDOLES
    DOBSON, D
    TODD, A
    GILMORE, J
    [J]. SYNTHETIC COMMUNICATIONS, 1991, 21 (05) : 611 - 617
  • [3] EPSTEIN RJ, 1988, LANCET, P521
  • [4] PREPARATION OF CARBOXYLIC AMIDES FROM ALDEHYDES BY OXIDATION
    GILMAN, NW
    [J]. JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1971, (14): : 733 - &
  • [5] The nitrosation of phenols Part VII Resorcinol monomethyl ether and m-cresol
    Hodgson, HH
    Clay, H
    [J]. JOURNAL OF THE CHEMICAL SOCIETY, 1929, : 2775 - 2778
  • [6] STRUCTURALLY MODIFIED ANTITUMOUR AGENTS .2. TOTAL SYNTHESIS OF A CYCLOPROPAMITOSENE
    JONES, GB
    MOODY, CJ
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (12): : 2455 - 2462
  • [7] JONES GB, 1989, THESIS U LONDON
  • [8] MAKOSZA M, 1988, LIEBIGS ANN CHEM, P203
  • [9] RADICAL MEDIATED OXIDATIONS IN ORGANIC-CHEMISTRY .3. AN EFFICIENT AND VERSATILE TRANSFORMATION OF ALDEHYDES INTO AMIDES
    MARKO, IE
    MEKHALFIA, A
    [J]. TETRAHEDRON LETTERS, 1990, 31 (49) : 7237 - 7240
  • [10] SYNTHESIS OF THE CARBAZOLE ALKALOID MURRAYAQUINONE-B
    MARTIN, T
    MOODY, CJ
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (02): : 241 - 246
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