The synthesis of novel antitumor antibiotics structurally related to the anthracyclinones
A practical synthesis of C(10)-functionalized derivatives of the anthracycline class of antitumor antibiotics is described. An efficient preparation of the tetracyclic epoxide 13 from the diquinone 8 and butadiene 9 yields a key intermediate for the stereospecific synthesis of the 7-deoxy aglycons 1...
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Published in | Journal of organic chemistry Vol. 55; no. 20; pp. 5520 - 5525 |
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Main Authors | , |
Format | Journal Article |
Language | English |
Published |
WASHINGTON
American Chemical Society
01.09.1990
Amer Chemical Soc |
Subjects | |
Online Access | Get full text |
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Summary: | A practical synthesis of C(10)-functionalized derivatives of the anthracycline class of antitumor antibiotics is described. An efficient preparation of the tetracyclic epoxide 13 from the diquinone 8 and butadiene 9 yields a key intermediate for the stereospecific synthesis of the 7-deoxy aglycons 14a-20a. The required cis-C(7)-hydroxy functionality is introduced stereospecifically to afford the aglycons 14b-20b. Finally, a high-yield coupling reaction to the duanosamine derivative 25 serves to both resolve the racemic aglycons and afford the targeted optically active anthracyclines 30 and 31. |
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Bibliography: | istex:C4A9A494A54606029195BA0F606E98C5CC15FFD5 ark:/67375/TPS-T8NBHLD4-K |
ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/jo00307a026 |