Abstract
Acetoxy-substituted triene(6) was synthesized from oleanolic acid(1) via methyl esterification of 17-carboxylic acid,benzoylation of 3-hydroxy,oxidation of 12-double bond by O3,dehydrogenation with Br2/HBr,enol acetylation of carbonyl group,and ring-C opening under UV light.Oxidations of compound 6 with different oxidants such as O3,meta-cholorperoxybenzoic acid(mCPBA),H2O2,t-BuOOH and Na2S2O8,yield decalin-type chiral synthons,epoxides,and/or lactone of oleanolic acid derivatives.
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