Synthesis and biological activity of 4′-azido- and 4′-trifluoracetamido-3′-chloro-3′-deamino-4′-deoxydaunorubicin

The syntheses of 1-O-acetyl-4-azido-3-chloro-L-lyxo-hexopyranose and 1-O-acetyl-3-chloro-4-trifluoracetamido-L-lyxo-hexopyranose are described. These aminosugars were successfully employed for the synthesis of 4′-azido- 3′-chloro-3′-deamino-4′-deoxydaunorubicin and 3′-chloro-3′-deamino-4′-deoxy-4′-trifluoracetamidodaunorubicin. The cytotoxicity of the above-mentioned compounds is discussed.