Anthracyclinones and the glycosidic anthracyclines are pigments, ranging in color from yellow to purple, which are produced by various species of Streptomyces (1, 2, 3). The very descriptive name anthracyclines was coined by Brockmann (1) and is derived from anthraquinones and the likewise tetracyclic tetracyclines. The antibiotic properties of the anthracyclines were observed soon after their discovery (for history see 4), but the compounds were far too toxic to be useful as antibiotics for treatment of infectious diseases. However, in the late sixties daunorubicin (1) was developed by Arcamone and his group at Farmitalia as well as MARAL at Rhône-Poulenc (4) into an anticancer drug especially successful in the treatment of acute leukemia. Today anthracyclines are among the most often used drugs in antitumor combination chemotherapy and the intensive research on their isolation and structure elucidation, pharmacology, biochemical mode of action as well as chemical synthesis is a result of their importance as antitumor drugs. It is therefore appropriate to demonstrate some of their structural properties on the most important members of the daunorubicin family: daunorubicin (1) and doxorubicin (2). The somewhat less cardiotoxic semisynthetic 4′-epi compounds (3) and (4) and the corresponding even more effective (but also more toxic) 4-demethoxy compounds (5) and (6) (idarubicins) obtained by chemical synthesis have also found use in clinical treatment (4, 5, 6, 7, 8).


Building Block Total Synthesis Asymmetric Synthesis Phthalic Ester Ceric Ammonium Nitrate 
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Copyright information

© Springer-Verlag/Wien 1989

Authors and Affiliations

  • K. Krohn
    • 1
  1. 1.Institut für Organische ChemieTechnischen UniversitätBraunschweigFederal Republic of Germany

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