• Studies directed towards the total synthesis of anthracycline antibiotics

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      https://www.ias.ac.in/article/fulltext/jcsc/093/06/1059-1078

    • Keywords

       

      Anthracyclines; antitumor antibiotics; adriamycin; daunomycin; daunomycinone; 4-demethoxydaunomycinone; 11-deoxydaunomycinone; L-daunosamine; 2-acetyl-2-hydroxy-5,8-dimethoxy 1,2,3,4-tetrahydronaphthalene

    • Abstract

       

      At present anthracycline antibiotics have proven to be the most exciting agents in cancer chemotherapy. Both adriamycin and daunomycin are proven to be effective against a variety of human tumour cells, despite their cardiotoxicity. However, some synthetic analogues, such as 4-demethoxydaunomycin, are shown to be better therapeutic ratios compared to adriamycin or daunomycin. Various approaches have been successfully made for the total synthesis of (±) 4-demethoxydaunomycinone, the aglycone of (±) 4=demethoxydaunomycin, starting from benzoquinone, napthalene or anthraquinone precursors. Finally an elegant approach for the stereoconvergent synthesis of (+) 4-demethoxydaunomycinone has been worked out.

      New methods involving both Diels-Alder and Friedal-Crafts acylation, have been developed for the total synthesis of daunomycinone and 11-deoxydaunomycinone. The synthesis of L-daunosamine, the amino sugar unit present in the antitumor anthracyclines has been successfully elaborated starting either from D-glucose or D-glucosamine.

    • Author Affiliations

       

      A V Rama Rao1

      1. National Chemical Laboratory, Pune - 411 008, India
    • Dates

       
  • Journal of Chemical Sciences | News

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