GB916790A - Steroids and the synthesis thereof - Google Patents

Abstract

The invention comprises steroid compounds of the general formula <FORM:0916790/IV (b)/1> wherein the 1,2-position is saturated or double bonded, R represents hydrogen and R1 represents a b -hydroxy group or together R and R1 represent an oxo group, X represents a halogen, Y represents hydrogen, and Z represents hydrogen or a hydroxy group, and the preparation thereof and of steroid compounds wherein Y represents a hydroxy group by treating steroid compounds of the general formula <FORM:0916790/IV (b)/2> wherein the 1,2-position is saturated or double bonded, R, R1, X and Z have the above significance, and Y1 represents hydrogen or a hydroxy or acyloxy group, with the oxygenation action produced by growing the microorganism Streptomyces roseochromogenus, e.g. by including the steroid reactant in an aerobic culture of the said microorganism, and the preparation of steroid compounds of the first general formula above wherein the 1,2-position is saturated or double bonded, R, p R1 and X have the above significance, Y represents hydrogen, and Z represents a hydroxy group, by reacting a steroid compound of the general formula <FORM:0916790/IV (b)/3> with osmium tetroxide, e.g. in the presence of an organic base such as pyridine, and reductively hydrolysing the resulting osmate ester, e.g. by treating the osmate ester with sodium sulphite or hydrogen sulphide. 16,17-Dehydro-steroids of the third general formula above, wherein the 1,2-position is saturated or double bonded, Y represents hydrogen, and R, R1 and X have the above significance, are prepared by treating steroid compounds of the first general formula above, wherein the 1,2-position is saturated or double bonded, Z represents hydrogen, and R, R1, X and Y have the above significance, with aluminium tertiary butylate at an elevated temperature. Specification 754,672 is referred to.