An expedient synthesis of [16,16,17-2H3]-epitestosterone via a one-pot deuteration and reduction of the 17-ketone followed by epimerization of a deuterated alcohol

Article abstract of DOI:10.1016/0040-4039(95)01623-P

The 17-Oxo group in androstane derivatives was reduced by sodium in deuterium oxide to [17-²H]-17β-alcohol. The 17β-tosyloxy group of 4 was found to be stable under the conditions of the i-steroid rearrangement. The S(N)2 reaction of 17β tosyla