Abstract
In order to examine the occurrence of "NIH shift"during hydroxylation of the aromatic steroid, 2-and 3-deuterio-3-deoxyestrones (IIIb, V) were synthesized as substrate. After oral administration of these labeled steroids to a rabbit, two principal metabolites, 2-hydroxy-3-deoxyestrone (Ib) and 17α-estradiol, were isolated from the collected urine specimen. Inspection of mass and nuclear magnetic resonance spectra revealed that aryl hydroxylation was accompanied by a migration of deuterium from the initially labeled site to an adjacent position. The direction and extent of isotope migration are listed in Table I.
