Oxidative cleavage of 3β-acetoxy-21-oxolup-18-en-28-oic acid by ruthenium tetroxide |
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| Authors: | M Kvasnica P Spacilova M Budesinsky M Hajduch J Sarek |
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| Institution: | (1) Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo n. 2, 166 10 Prague 2, Czech Republic;(2) Laboratory of Experimental Medicine, Departments of Pediatrics and Oncology, Faculty of Medicine, Palacky University in Olomouc, Puskinova 6, 77520 Olomouc, Czech Republic;(3) Department of Organic Chemistry, Faculty of Science, Palacky University in Olomouc, Trida Svobody 8, 77200 Olomouc, Czech Republic; |
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| Abstract: | 3β-Acetoxy-21-oxolup-18-en-28-oic acid was used as a starting compound for oxidative cleavage by ruthenium tetroxide generated
in situ from ruthenium dioxide by sodium metaperiodate in a biphasic system. Tricyclic and tetracyclic acids of baccharane type were
prepared by this reaction, and their structures were confirmed using spectral data. These acids were further used for synthesis
of appropriate methyl and acetoxymethyl esters. All prepared compounds were tested on cytotoxic activity against CEM tumor
cell line, and several compounds showed activity in low micromolar concentrations. |
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