Boar taint steroid derivatives for immunological studies. Synthesis of 11 α-hydroxy-5α-androst-16-en-3-one and its hemisuccinate

Abstract

5α-Androstane-3,11,17-trione has been converted into the title alcohol in five steps in an overall yield of 42%. Selective acetalization at C-3 allowed the use of the vinyl iodide route for introduction of the double bond at C-16,17 by transformation of the 17-oxo group. Reduction of the intermediate 17-iodo-16-ene with sodium in ethanol took place with concomitant reduction of the 11-oxo group to the 11α-alcohol. Esterification with succinic anhydride in pyridine gave the 11α-yl hemisuccinate.