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Abstract

Irradiation of 1-dehydro-4-methyl-testosterone (IV) in dioxane solution affords as a single product an isomer, which on the basis of extensive degradation is shown to possess structure V. A similar photochemical transformation leads from 1-dehydro-2,4-dimethyl-testosterone (XXXVII) to the corresponding lumiproduct XXXVIII. Since it has been previously shown that 1-dehydro-testosterone (III) under the same conditions yields a mixture of 8 compounds, it appears now that the photochemical isomerisation of cross-conjugated steroidal dienones is profoundly affected by the presence of a methyl substituent at C-4.