Isotopic labelling experiments using [16α-2H]-3β,16β-dihydroxy-5α-androstan-17-one (1) show that an intramolecular 1,2-hydride shift mechanism is operative in its rearrangement to the corresponding 17β-hydroxy-16-one with both base and acid.
M. Numazawa and M. Nagaoka, J. Chem. Soc., Chem. Commun., 1982, 530 DOI: 10.1039/C39820000530
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