Anhydrous HF transforms cholesterol into the two epimeric 17β-hydroxy-3-methyl-3-(4-fluoro-4-methyl)pent-1-yl-D-homo-5α-androstanes, through a backbone rearrangement followed by ring-expansion and hydride transfer.
P. Bourguignon, J. C. Jacquesy, R. Jacquesy, J. Levisalles and J. Wagnon, J. Chem. Soc. D, 1970, 349 DOI: 10.1039/C29700000349
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