New steroid compounds and method for the transformation of epoxy-ketones by the action of fermenting yeast

摘要

The invention comprises pregnan-3,4,5-triol-20 - one, 17b - methyl - 18 - nor - D 4,13 - 17a -pregnadiene-16a , 20-diol-3-one, its diacetate, 17b - methyl - 18 - nor - D 5,13 - 17a - pregnadiene - 3b ,16a ,20 - triol, its triacetate, 17b -methyl - 18 - nor - D 13 - 17a - pregnene - 16a , 20-diol-3-one and 17b -methyl-18-nor- D 5,13-17a -pregnadiene - 3b ,16a ,20,21 - tetrol 21 - acetate, together with processes for converting an a ,b -epoxyketone to a polyhydric compound having hydroxyl groups attached to the a - and b -carbon atoms and in which the carbonyl group is reduced to a secondary hydroxyl group, and for converting an a -b -epoxy-ketone of partial formula: FORM:0813317/IV (b)/1 (where R is alkyl containing not more than four carbon atoms or an acylated hydroxyalkyl group) especially a 16 : 17 - oxido - 20 - keto steroid, into the corresponding molecularly rearranged unsaturated diol of partial formula: FORM:0813317/IV (b)/2 by the action of fermenting yeast in each case. In examples: (1) benzalacetophenone epoxide in ethanol is added to fermenting yeast and the mixture left for 10 days at 32 DEG C., adding more yeast at 48 hour intervals; 1,3-diphenylglycerol is then isolated by extraction with ethyl acetate; (2) 4,5-epoxy-pregnan-3,20-dione is treated with yeast as in (1), giving pregnane-3,4,5-triol-20-one; similarly (3) 16,17- epoxy - progesterone gives 17b - methyl - 18 - nor - D 4,13 - 17a - pregnadiene - 16a ,20 - diol-3-one, characterized as its diacetate; (4) 16,17-epoxy - D 5 - pregnen - 3b - ol - 20 - one yields 17b - methyl - 18 - nor - D 5,13 - 17a - pregnadiene-3b ,16a ,20-triol and then the triacetate; (5) 16,17 - epoxy - pregnane - 3,20 - dione gives 17b - methyl - 18 - nor - D 13 - 17a - pregnene-16a ,20 - diol - 3 - one; and (6) 16,17 - epoxy-D 5 - pregnene - 3b ,21 - diol - 20 - one - 21 - acetate yields 17b -methyl-18-nor- D 5,13-17a -pregnadiene-3b ,16a ,20, 21-tetrol 21-acetate.