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Menthofuran is an organic compound found in a variety of essential oils including that of Pennyroyal. It is highly toxic and believed to be the primary toxin in Pennyroyal responsible for its potentially fatal effects. After ingestion of menthofuran, it is metabolically activated to chemically reactive intermediates that are hepatotoxic.
Methofuran is produced biosynthetically from pulegone by the enzyme menthofuran synthase.
Synthesis
Menthofuran was synthesized from 5-methylcyclohexane-1,3-dione and allenyldimethylsulfonium bromide in two steps via a novel furannulation strategy consisting of enolate addition and rearrangement.
References
Menthofuran Wikipedia(Text) CC BY-SA