SYNTHESIS OF [C-14] ANTHRACYCLINE ANTICANCER AGENT -O-(2',6'-DIDEOXY-2'-FLUORO-ALPHA-L-TALOPYRANOSYL) ADRIAMYCINONE-14-C-14(DA-125-C-14)

Synthesis of the anthracycline anticancer agent, -O-(2',6'-dideoxy-2'- fluoro-alpha-L-talopyranosyl) Adriamycinone (DA-125-C-14) labeled with carbon-14 regiospecifically for ADME (absorption, distribution, metab olism, and excretion) studies is described. Unlabeled 7-O(2',6'-dideox y-2'-fluoro-alpha-L-talopyranosyl) adriamycinone (Dong-A Pharm. Lot Ml -8008) (B-1) was employed as the starting material in this nine-step r adiosynthesis. The C-14-labeled N-methyl-N-nitroso-p-toluene sulfonami de (methyl-C-14), prepared in five steps from (14)CH(3)l, served as th e source of the label. A total of 335 mu Ci of 14-C-14-DA-125 (specifi c activity 6.63 mCi/mmol, radiochemical purity of 98%, and overall iso lated radiochemical yield >1 % based on N-methyl-C-14-N-nitroso-p-tolu enesulfonamide,A-5) was prepared.