Collect. Czech. Chem. Commun. 1985, 50, 2753-2759

Oxidation of 19β,28-epoxy-18α-oleanan-3-one and -1-one with peracids

Jan Sejbal, Jiří Klinot, Daniela Hrnčířová and Alois Vystrčil

Department of Organic Chemistry, Charles University, 128 40 Prague 2


The reaction of 3-oxo derivative I and 1-oxo derivative XII of 19β,28-epoxy-18α-oleanane with peracids leads to corresponding lactones II or XIII, respectively, which were converted to A-seco acids III, V, and XIV and esters IV, VI, VII, and XV. Under acid catalysis oxidation of ketone I results in the degradation of one methyl group in position 4 and formation of compounds VIII and IX. On reaction with 3-chloroperbenzoic acid the α,β-unsaturated ketone XVI gives epoxyketone XVII.