Intramolecular 1,2-hyride shift in the rearrangement of steroidal 16β-hydroxy-17-ones to 17β-hydroxy-16-ones
Abstract
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.