8-Hydroxyanthracyclinones from .epsilon.-rhodomycinone
- 1 November 1980
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Medicinal Chemistry
- Vol. 23 (11) , 1242-1244
- https://doi.org/10.1021/jm00185a020
Abstract
.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. 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.This publication has 3 references indexed in Scilit:
- Adriamycin analogs. 3. Synthesis of N-alkylated anthracyclines with enhanced efficacy and reduced cardiotoxicityJournal of Medicinal Chemistry, 1979
- Adriamycin analogs. 2. Synthesis of 13-deoxyanthracyclinesJournal of Medicinal Chemistry, 1978
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