| Abstract
| - trans,trans-1-(Aminomethyl)-2-methoxy-3-phenylcyclopropane(3) was synthesized in three stepsfrom (Z)-β-methoxystyrene and ethyl diazoacetate.Compound 3 was shown to be a substrate andinactivator of mitochondrial beef liver monoamine oxidase (MAO) with apartition ratio of 1428.MAO-catalyzed oxidation of 3 produces one majormetabolite, isolated and identified by GCOSY,GHMQC, and GHMBC NMR techniques to betrans,trans-2-methoxy-3-phenyl-1-N-[(3-phenyl-N-pyrrolyl)methyl]cyclopropane (7). Amechanism, supported by a model reaction, is proposed forthe formation of this metabolite.
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