Steroids. Part XXVIII. The structure of digacetigenin: comparative experiments with ruscogenin and related compounds

Abstract

The 1β-acetoxyl group of ruscogenin diacetate is not hydrolysed by potassium hydrogen carbonate at 20°. Ruscogenin diacetate by extended treatment with methanolic hydrocholoric acid at 65° gave ruscogenin unaccompanied by a 1-methyl-1(10),5-dienic rearrangement product. Ruscogenin by oxidation with chromic acid in acetone at 10° gives successively the 1β-hydroxy-5-en-3-one and the 5-ene-1,3-dione, converted by methanolic hydrochloric acid into the 4-ene-1,3-dione and its 1-methyl enol-ether; ruscogenin by Oppenauer oxidation gives, by way of the 1β-hydroxy-4-en-3-one, the 1,4-dien-3-one.