- THE OXIDATION OF PROGESTERONE UNDER GoAggIII CONDITIONS
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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.
- Barton, Derek H. R.,Doller, Dario
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p. 984 - 990
(2007/10/02)
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