8-Hydroxyanthracyclinones from ε-Rhodomycinone

Article abstract of DOI:10.1021/jm00185a020

ε-Rhodomycinone was converted into 8,9-dehydro-ζ-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 η-rhodomycinone derivative, with only small amounts of the diols.None of the new rhodomycinones were active against Bacillus subtilis, but 8,9-dehydro-ζ-rhodomycinone was active in the induction of lytic phage in Escherichia coli.