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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Bibliographic Details
Published inJournal of organic chemistry Vol. 55; no. 20; pp. 5520 - 5525
Main Authors Confalone, Pat N, Pizzolato, Giacomo
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.09.1990
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Condensed benzenic and aromatic compounds
Exact sciences and technology
Organic chemistry
Physical Sciences
Preparations and properties
Science & Technology
Anthracyclinones
Phenols
Aromatic compound
Tetracyclic compound
Aglycone
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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.
Bibliography:istex:C4A9A494A54606029195BA0F606E98C5CC15FFD5
ark:/67375/TPS-T8NBHLD4-K
ISSN:0022-3263
1520-6904
DOI:10.1021/jo00307a026