Collect. Czech. Chem. Commun. 1984, 49, 313-319

7-O-Alkyl derivatives of daunomycinone

Věra Přikrylová, Petr Sedmera, Josef V. Jizba, Jindřich Vokoun, Helena Lipavská, Miloslav Podojil and Zdenko Vaněk

Institute of Microbiology, Czechoslovak Academy of Sciences, 142 20 Prague 4


Reaction of daunomycinone (I) with alcohols and p-toluenesulfonic acid produces a mixture (~3 : 1) of its (7S)- and (7R)-O-alkyl derivatives II-IX. According to the 1H NMR evidence, the alicyclic ring exists in the 9H8 conformation in (7R)-O-alkyl derivatives, on the contrary to (7S)-epimers and 7-epi-daunomycinone that adopt the 8H9 conformation.