GB975596A - Preparation of steroids and d-homo-steroids related to oestrone - Google Patents

Abstract

Compounds of formula <FORM:0975596/C1/1> or <FORM:0975596/C1/2> wherein each R is H or alkyl, R1 is alkyl, Q is methylene or ethylene, Y is carbonyl, hydroxymethylene or a group convertible by hydrolysis into carbonyl or hydroxymethylene and E is a group (such as alkoxy, hydroxy, acyloxy, acylamino, amino, monoalkylamino or dialkylamino) which activates the aromatic ring in electrophilic substitution and is predominantly o- and p-directing, are produced by cyclodehydration of a compound of structure <FORM:0975596/C1/3> e.g. by use of an acid catalyst. H in the formula is preferably trans. to R1. In examples, D-homo-8- and -9(11)-dehydro-oestrone methyl ethers (R=H, R1=methyl, Q=ethylene, Y=carbonyl, E=methoxy) were prepared and converted by reduction to O-homo oestradiol methyl ether, which was oxidised to D-homo oestrone methyl ether for identification; the analogous methyl ethers of 9(11)-dehydro-oestrone, oestradiol and oestrone were similarly made. Dehydrooestradiol methyl ether was prepared directly from the starting material in which Y is hydroxymethylene and was hydrogenated to oestradiol methyl ether. Specifications 975,591, 975,592, 975,593 and 975,594 also are referred to.