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Attempted epoxidation of the cyclohexenyl carboxylic acid 11 using m-chloroperoxybenzoic acid was accompanied by epoxide ring-opening and gave a mixture of lactones 13, 14 and 15, ratio 20 : 40 : 40, respectively. In contrast, treatment of the cis-hydroxyepoxide 18 of the methyl ester 12 with aqueous sulfuric acid in acetonitrile gave the lactone 14 with excellent regioselectivity together with the triol 22. The trans-hydroxyepoxide 19 gave only the lactone 14 under these conditions.

An observation on the regioselectivity of ring-opening of some substituted cyclohexenyl epoxides