GB763202A - Polyhydrophenanthrene compounds - Google Patents

Abstract

The invention comprises (1) dodecahydrophenanthrones of formula <FORM:0763202/IV(b)/1> in which the 7-position is occupied either by a bivalent group convertible to keto by acid hydrolysis (e.g. a cyclic ketal group) or by a pair of univalent groups together convertible to a single keto group by acid hydrolysis (e.g. a noncyclic ketal grouping); (2) decahydrophenanthrones of formula <FORM:0763202/IV(b)/2> in which the 7-position is occupied by a univalent group convertible to keto by acid hydrolysis (e.g. an enol ether group); and (3) dodecahydrophenanthrones of formula <FORM:0763202/IV(b)/3> wherein, in each formula, R1 represents a hydroxy, keto or acyloxy group and R2 an acyl or carboalkoxy group. Compounds (1) and (2) are prepared by reacting the corresponding compounds in which R2 represents hydrogen with an ester (e.g. methyl carbonate, formate or acetate) in the presence of an alkaline condensing agent (e.g. sodium hydride, amide or alkoxide) and preferably in presence of an alcohol or hydrocarbon solvent. Compounds of formula (3) are prepared by acid hydrolysis of compounds (1) and (2). The examples describe the preparation of 2-formyl-4-hydroxy-, 2-acetyl-4-hydroxy -, 2 - hydroxymethylene - 4 - hydroxy -, 2 - acetyl - 4 - acetoxy -, 2 - formyl - 4 - keto -, 2 - acetyl - 4 - keto - and 2 - carbomethoxy - 4 - keto - 4b - methyl - 7 - ethylenedioxy - 1:2:3:4: 4a:4b:5:6:7:8:10:10a - dodecahydrophenanthrene-1-one; 2-formyl-4-hydroxy-, 2-acetyl-4-hydroxy-, 2-hydroxymethylene-4-hydroxy-, 2 - formyl - 4 - keto -, 2 - acetyl - 4 - keto - and 2 - carbomethoxy - 4 - keto - 4b - methyl - 1:2:3: 4:4a:4b:5:6:7:9:10:10a - dodecahydrophenanthrene-1:7-dione. Specifications 763,207, 763,208 and 763,210 are referred to.