Synthesis of ring A fluorinated anthracyclines

Article abstract of DOI:10.1016/0040-4020(95)00892-C

The synthesis of different anthracyclines of the daunorubicin family, fluorinated at position 8 or 10 is described. The 8-fluoroderivatives (2a-c) were obtained by glycosylation of the corresponding fluorinated aglycones. The 10-fluoroderivatives (2d-g) were synthesized directly from daunorubicin (1a) and idarubicin (1c) following a non deglycosidative approach. 8-(S)-Fluorodoxorubicin was obtained from 8-(S)-fluorodaunorubicin, although in very low yield. Copyright