Studies on the alkali-induced epimerisation at position 2 in 2-hydroxygibbane 1 → 4a lactones are reported. Mechanisms involving fission of the C-2-oxygen or C-2-hydrogen bonds are ruled out. The 2-methoxygibbane 1 → 4a lactones are not epimerised, indicating the abstraction of a proton from the 2-hydroxyl group as required in the originally suggested retro-aldol mechanism. Attempts to trap the intermediate were unsuccessful.
J. MacMillan and R. J. Pryce, J. Chem. Soc. C, 1967, 740 DOI: 10.1039/J39670000740
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