The thermal decarboxylation of peroxycholanic acid (1) leads by a radical chain reaction, to the epimeric 16-hydroxy, norcholanes (2) in > 35% yield; this regio-selective D-ring functionalization is the result of an intra-molecular homolytic 1,5-hydrogen shift.
J. Bégué, D. Lefort and T. D. Thac, J. Chem. Soc., Chem. Commun., 1981, 1086 DOI: 10.1039/C39810001086
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