Studies directed towards the total synthesis of anthracycline antibiotics |
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Authors: | A. V. Rama Rao |
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Affiliation: | (1) National Chemical Laboratory, 411 008 Pune, India |
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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. |
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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 |
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