GB1264050A - Steroidal lactones - Google Patents

Abstract

1,264,050. Steroidal lactones. AMERICAN HOME PRODUCTS CORP. 24 Feb., 1970 [24 Feb., 1969], No. 8942/70. Heading C2U. Novel steroids of the partial Formula (I) (wherein Q represents the remaining A, B and C rings of a steroid nucleus of the androstane or estrane series) are prepared by NaBH 4 reduction of steroids of the partial formula (wherein R<SP>1</SP> is H or C 2-4 acyl), prepared in turn by treatment of steroids of the partial formula with an organic peracid in the presence of a nucleophilic reagent to give products wherein OR<SP>1</SP> is hydroxy, with, when required, subsequent acylation to give products wherein OR<SP>1</SP> is acyloxy. Products containing a 3-hydroxy group may be acylated by standard procedures. Preferred products have the formulµ (where R is H, C 1-4 alkyl, C 5-6 cycloalkyl or C 2-4 acyl), and novel intermediates are those corresponding to the 7α,8α-epoxides and containing an OR<SP>1</SP> group in the lactone ring. These intermediates may be prepared from 17#- hydroxy - 17α - (3<SP>1</SP> - furyl) starting materials already containing the 7α,8α-epoxy group or from corresponding materials containing a #<SP>7</SP> double bond. Equilin 3 - methyl, - ethyl, - propyl, - isopropyl, - n - butyl, - sec. - butyl, - cyclopentyl and -cyclohexyl ethers are prepared from the sodium or potassium salt of equilin and the appropriate alkyl or cycloalkyl halides. These and the corresponding tetrahydropyranyl ether are converted to the corresponding 7α,8α- epoxy compounds by treatment with m-chloroperbenzoic acid. Starting materials of the partial Formula (V) are prepared from the corresponding 17-ones, 3-iodofuran and n-butyl-lithium; hydrolysis of the 3-tetrahydropyranyl ether of 7α,8α-epoxy- 17α - (3<SP>1</SP> - furyl) - 3 - hydroxyestra - 1,3,5(10)- trien-17-ol gives the free 3-ol, which on acylation is converted to 3-acylates e.g. the acetate, propionate and butyrate. The novel steroidal lactones of the partial Formula (I) possess estrogenic activity, and they may be made up into pharmaceutical compositions with suitable carriers.