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Abstract
The oxidation of pregn-4-ene-3,20-dione (progesterone) by the GoAggIII system (aqueous hydrogen peroxide, ferric chloride, picolinic acid in pyridine-acetic acid solution) has been investigated. Two tri-keto derivatives were isolated and identified as pregn-4-ene-3,6,20-trione and pregn-4-ene-3,12,20-trione. The third major product isolated was identified as the unstable 5α-formyl-A-nor-pregnane-3,20-dione, which deformylated spontaneously to A-nor-5β-pregnane-3,20-dione. A mechanism for the A-ring contraction is proposed, based upon the participation of a carbon-Fe(V) intermediate.
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