Oxyhalogenation of glycals for the synthesis of anti-tumor-active 2'-halo daunorubicin analogs.

Article abstract of DOI:10.1016/0008-6215(85)85212-5

Alkoxyhalogenation of L-rhamnal diacetate with daunomycinone and N-iodosuccinimide afforded 37% of 7-O- (3,4-di-O-acetyl-2,6-dideoxy-2-iodo-alpha-L-mannopyranosyl)daunomycin one (4, NSC 331,962) and 7% of the beta-L-gluco analog (NSC 353,457); a similar procedure with L-fucal diacetate gave 77% of 7-O-(3,4-di-O-acetyl-2,6-dideoxy-2-iodo-alpha-L-talopyranosyl) daunomycinone (NSC 327,472). Compound 4 showed high activity (T/C 247) and low toxicity in the P-388 lymphocytic leukemia screen in mice.