Monoamine Oxidase-Catalyzed Oxidative Rearrangement of trans,trans-1-(Aminomethyl)-2-methoxy-3-phenylcyclopropane

Xingliang Lu*, Shengtian Yang, Richard B. Silverman

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

3 Scopus citations


trans,trans-1-(Aminomethyl)-2-methoxy-3-phenylcyclopropane (3) was synthesized in three steps from (Z)-β-methoxystyrene and ethyl diazoacetate. Compound 3 was shown to be a substrate and inactivator of mitochondrial beef liver monoamine oxidase (MAO) with a partition ratio of 1428. MAO-catalyzed oxidation of 3 produces one major metabolite, isolated and identified by GCOSY, GHMQC, and GHMBC NMR techniques to be frans,frarcs-2-methoxy-3-phenyl-l-Ar-[(3-phenyl-JV-pyrrolyl)methyl]cyclopropane (7). A mechanism, supported by a model reaction, is proposed for the formation of this metabolite.

Original languageEnglish (US)
Pages (from-to)8961-8966
Number of pages6
JournalJournal of Organic Chemistry
Issue number25
StatePublished - 1996

ASJC Scopus subject areas

  • Organic Chemistry


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