1999 antibiotics

antibioticsU 1200

42 - 264Synthesis and Antitumor Activity of 7-O-[2,6-Dideoxy-2-fluoro-5-C- (trifluoromethyl)-α-L-talopyranosyl]-daunomycinone and -adriamycinone. — The title compounds (XVI) and (XVII) are prepared bycoupling of glycosyl iodide (XIV) with daunomycinone (XV). The key steps inthis route are the regioselective fluorination of α-D-lyxopyranoside (I) yieldingthe β-L-ribopyranoside (II) and the trifluoromethylation of L-ribose derivative(VIII) yielding the L-altritol derivative (X). The daunorubicin-type analogue(XVI) shows low activity while the doxorubicin-type analogue (XVII) exhibitsa slightly higher activity than the reference compound. — (NAKAI, KEN;TAKAGI, YASUSHI; TSUCHIYA, TSUTOMU; Carbohydr. Res. 316 (1999)1-4, 47-57; Inst. Bioorg. Chem., Nakahara, Kawasaki 211, Japan; EN)

1

1999 antibiotics

2