GB763205A - Polyhydrophenanthrene compounds - Google Patents

Abstract

The invention comprises (1) dodecahydrophenanthrones of formula <FORM:0763205/IV(b)/1> in which the 7-position is occupied either by a divalent group (e.g. a cyclic ketal group) or a pair of univalent groups (e.g. a non-cyclic ketal group) both types being convertible to a single keto group by acid hydrolysis; (2) decahydrophenanthrones of formula <FORM:0763205/IV(b)/2> in which the 7-position is occupied by a univalent group (e.g. an enol ether group) convertible to keto by acid hydrolysis; (3) dodecahydrophenanthrones of formula <FORM:0763205/IV(b)/3> wherein, in each formula, R1 is a keto, hydroxy or acyloxy group and R2 is an acyl or carboalkoxy group. The compounds are prepared by reacting compounds of formul <FORM:0763205/IV(b)/4> <FORM:0763205/IV(b)/5> with a methyl halide in presence of an alkali and, if desired, subjecting the products to acid hydrolysis. Preferred starting materials are those described in Specification 763,202. The methylation is preferably effected by adding the starting material to a suspension of potassium carbonate in acetone, adding excess methyl iodide and stirring the mixture at room temperature. Products having a 4-acyloxy substituent may be hydrolysed to the corresponding 4-hydroxy compounds, and the latter may be oxidized to the corresponding 4-keto compounds by treatment with a pyridine/chromium trioxide complex as described in Specification 733,808. The examples describe the preparation of 2 - formyl - 4 - hydroxy -, 2 - acetyl - 4 - hydroxy -, 2 - acetyl - 4 - acetoxy -, 2 - formyl - 4 - keto -, 2 - carbomethoxy - 4 - keto - and 2 - acetyl - 4 - keto - 2 : 4b - dimethy) - 7 - ethylenedioxy - 1 : 2 : 3 : 4 : 4a : 4b : 5 : 6 : 7 : 8 : 10 : 10a - dodecahydrophenanthrene - 1 - ones ; 2 - formyl - 4 - hydroxy -, 2 - acetyl - 4 - hydroxy -, 2 - formyl - 4 - keto -, 2 - carbomethoxy - 4 - keto - and 2 - acetyl - 4 - keto - 2 : 4b - dimethyl - 1 : 2 : 3 : 4 : 4a : 4b : 5 : 6 : 7 : 9 : 10 : 10a - dodecahydrophenanthrene - 1 : 7-diones. Specifications 763,206 and 763,208 also are referred to.