GB979027A - - Google Patents

Abstract

The invention comprises steroids of the general formula <FORM:0979027/C1/1> wherein R and R1 are the same or different and represent alkyl groups containing 1 to 10 carbon atoms, the group <FORM:0979027/C1/2> represents <FORM:0979027/C1/3> and R2 represents a hydrogen atom or a carboxylic acyl group, and R3 represents a carboxylic or sulphonic acyl group, and a process for the preparation of steroids of the above general formula wherein R, R1 and <FORM:0979027/C1/4> have the above significance and R2 and R3 are the same or different and each represents a hydrogen atom or a carboxylic acyl group, and R3 may also represent a sulphonic acyl group, by dehydrogenating steroids of the general formula <FORM:0979027/C1/5> wherein R, R1, R2 and R3 have the significance indicated immediately above, with selenium dioxide or with a culture of Corynebacterium simplex, Bacillus Sphaericus, or Didymella lycopesici. The above process may be modified in that a product containing a 9-unsubstituted-11a -hydroxy grouping may be either oxidized to the corresponding 11-keto compound or acylated to form the required 11a -acyloxy or sulphonyloxy compound such as the 11a -acetoxy or p-toluenesulphonyloxy compound; the 11a -p-toluenesulphonyloxy compound may be converted into the corresponding D 1,4,9(11)-compound by splitting of the p-toluenesulphonyloxy group for example, with sodium acetate in boiling acetic acid; the D 1,4,9(11)-compound may be reacted with N-bromoacetamide in tetrahydrofuran to form the 9a -bromo-11b -hydroxy compound; and the latter compound may be treated with aqueous caustic alkali to form the corresponding 9, 11b -epoxide. Specification 873,300 is referred to.