Synthesis of 14β-Pregnanes and Selenium Dehydrogenation of 3β, 14β-Dihydroxy-5α, 17α-pregnane-15, 20-dione 3-Aceate. Studies on C-Nor-D-homosteroids. VI.

Abstract

The synthesis of some C/D cis-15-ketopregnane derivatives from hecogenin is described. Hecogenin was degraded to II which in turn was converted to V via III. Catalytic hydrogenation of V affords the five reduction products, VIII to XIII. VIII was dehydrogenated with selenium but Jacobs' hydrocarbon was not obtained.