Collect. Czech. Chem. Commun. 1984, 49, 653-665

Reaction of daunomycinone with diols

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

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


During the acid catalyzed acetalization of the 13-ketone group of daunomycinone (I) by 1,2-ethanediol or 1,3-propanediolits 7-O-alkylation also takes place. The 7-O-ω-hydroxyalkyl derivatives only are formed with 1,4-butanediol, 1,6-hexanediol or 1,4-butynediol. The conformational preference of new compounds is discussed. The (7S)-ω-hydroxyalkyl derivatives of daunomycinone are active against Bacillus subtilis, on the contrary to I and their (7R)-epimers.