A synthesis of 2,2-dimethylcholesterol (VI) from 5α-cholestan-3-one is described. Solvolysis of the methane-sulphonate of (VI) gives as the major product the corresponding cycloalcohol, 2,2-dimethyl-3α,5-cyclo-5α-cholestan-6β-ol. Apparently the cationic product-determining intermediate reacts predominantly by co-ordination with solvent at C-6.
S. R. Pathak and G. H. Whitham, J. Chem. Soc. C, 1968, 193 DOI: 10.1039/J39680000193
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