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

Xingliang Lu; Shengtian Yang; Richard B. Silverman

doi:10.1021/jo961540a

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

J Org Chem. 1996 Dec 13;61(25):8961-8966. doi: 10.1021/jo961540a.

Authors

Xingliang Lu¹, Shengtian Yang, Richard B. Silverman

Affiliation

¹ Department of Chemistry and Department of Biochemistry, Molecular Biology, and Cell Biology, Northwestern University, Evanston, Illinois 60208-3113.

PMID: 11667878
DOI: 10.1021/jo961540a

Abstract

trans,trans-1-(Aminomethyl)-2-methoxy-3-phenylcyclopropane (3) was synthesized in three steps from (Z)-beta-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 trans,trans-2-methoxy-3-phenyl-1-N-[(3-phenyl-N-pyrrolyl)methyl]cyclopropane (7). A mechanism, supported by a model reaction, is proposed for the formation of this metabolite.