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

Abstract

C-3 allowed the use of the vinyl iodide route for introduction of the double bond at C-16,17 by transformation of the 17-0x0 group. Reduction of the intermediate 17-iodo-16-ene with sodium in ethanol took place with concomitant reduction of the 11 -ox0 group to the 1 1 a-alcohol. Esterification with succinic anhydride in pyridine gave the 1 1 ~-y l hemisuccinate.