GB764324A - Cyclopentanopolyhydrophenanthrene compounds - Google Patents

Abstract

The invention comprises D 7(8) or 8(14)-11-keto-cyclopentanopolyhydrophenanthrene compounds which compounds (a) are obtainable by reacting a D 8(9)-7,11-dihalogeno-cyclopentanopolyhydrophenanthrene compound having at rings B and C the formula <FORM:0764324/IV(b)/1> wherein X represents a halogen, with an aqueous solution of a metal salt which has a cation that forms water-insoluble halides and an anion that does not react with the cyclopentanopolyhydrophenanthrene compound, and (b) have at rings B and C one of the following formul <FORM:0764324/IV(b)/2> and <FORM:0764324/IV(b)/3> and the preparation thereof by the above process. Suitable metal salts that may be used are sliver nitrate and mercurous nitrate. The process may be carried out in a water-miscible organic solvent such as acetone. The above D 7(8) or 8(14)-11-keto compounds may be converted into D 8(9)-11-keto-cyclopentanopolyhydrophenanthrene compounds by treatment with a base, e.g. an alkali metal hydroxide, an alkali - earth metal hydroxide, ammonium hydroxide or an organic base such as a tertiary organic base-particularly pyridine. The bases are preferably used in aqueous solution. D 7(8)-or 8(14) - 11 - keto - cyclopentanopolyhydrophenanthrene compounds as defined above which may be prepared are D 7(8),22 or 8(14),22-11-keto-ergostadiene and the corresponding 3-acetoxy compound, D 7(8) or 8(14)-11-keto-cholestene and the corresponding 3-acetoxy compound, D 7(8),22 or 8(14),22 - 3 - acetoxy - 11 - keto - stigmastadiene, D 7(8) or 8(14) - 3 - acetoxy - 11 - keto - cholenic, and -bisnorallocholenic acid, D 7(8) or 8(14) - 3 - acetoxy - 11,20 - diketo - allopregnene, and D 7(8) or 8(14) - 11 - keto - dehydrotigogenin acetate. One detailed example is given.