Under acidic conditions in ethanol the side-chain of (23S)-lanosta-8,24-3β,23-diol undergoes an allylic rearrangement to yield lanosta-8,24-diene-3β,25-diol, 25-ethoxylanosta-8,23-dien-3βol, and (23S)- and (23R)-23-ethoxylanosta-8,24-dien-3β-ol. Under stronger acid conditions, loss of the elements of water from the side chain occurs to give lanosta-8,22,24-trien-3β-ol.
N. Entwistle and A. D. Pratt, J. Chem. Soc., Perkin Trans. 1, 1973, 1235 DOI: 10.1039/P19730001235
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