The mechanism of cytochrome P450-catalyzed allylic hydroxylation was found to be consistent with a hydrogen abstraction-oxygen rebound mechanism by Groves and Subramanian.47 A consequence of generating a radical intermediate, as the mechanism requires, is the possible production of a rearranged product. This is seen in the metabolism of (R)-pulegone (18), the major constituent of pennyroyal oil, a volatile plant oil that has been used as an abortifacient and causes major toxicity at high doses. Menthofuran (19), previously identified as a metabolite of pulegone, appeared to arise from initial cytochrome P450-catalyzed oxidation of one of the allylic methyl groups.48 To probe the mechanism of the reaction, the (E)-methyl-d3 analog of pulegone (18) was synthesized and incubated with o cd,
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