Synthesis and antitumor activity of 7-O-[2,6-dideoxy-2-fluoro-5-C-(trifluoromethyl)-α-l-talopyranosyl]-daunomycinone and -adriamycinone

7-O-[2,6-Dideoxy-2-fluoro-5-C-(trifluoromethyl)-α-l-talopyranosyl]-daunomycinone and -adriamycinone have been prepared by the coupling of 3,4-di-O-acetyl-2,6-dideoxy-2-fluoro-5-C-(trifluoromethyl)-α-l-talopyranosyl iodide with daunomycinone. The key steps in this synthesis are the regioselective fluorination of methyl α-d-lyxopyranoside to give the 4-deoxy-4-fluoro-β-l-ribopyranoside and the C-trifluoromethylation of the aldehydo-l-ribose derivative to give the 1,1,1-trifluoro-5-monofluoro-l-altritol derivative. Antitumor activities of the synthetic products were compared with those for the 2′-deoxy-2′-fluoro and 2′,6′-dideoxy-5′-C-trifluoromethyl analogs.