8-Hydroxyanthracyclinones from epsilon-rhodomycinone.
epsilon-Rhodomycinone was converted into 8,9-dehydro-zeta-rhodomycinone, which gave a cis diol with osmium tetroxide and a pair of epimeric epoxides with m-chloroperbenzoic acid. Acid-catalyzed opening of the epoxides gave the corresponding trans diols. In contrast, acid treatment of the trimethyl ethers of these epoxides gave predominantly a lactone and an eta-rhodomycinone derivative, with only small amounts of the diols. None of the new rhodomycinones were active against Bacillus subtilis, but 8,9-dehydro-zeta-rhodomycinone was active in the induction of lytic phage in Escherichia coli.
D018943:Anthracyclines; D001412:Bacillus subtilis / Q000187:drug effects; D003090:Coliphages / Q000187:drug effects; D009279:Naphthacenes / Q000138:chemical synthesis* / Q000494:pharmacology; D014775:Virus Activation / Q000187:drug effects
D018943:Anthracyclines; D009279:Naphthacenes; C015490:rhodomycinone