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 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 daunosamine derivative 25 serves to both resolve the racemic aglycons and afford the targeted optically active anthracyclines 30 and 31. © 1990, American Chemical Society. All rights reserved.