The Kulinkovich Reaction in the Synthesis of Constrained N,N-Dialkyl Neurotransmitter Analogues
Catherine A. Faler and Madeleine M. Joulliť*
*Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, Email: mjoulliesas.upenn.edu
C. A. Faler, M. M. Joulliť, Org. Lett., 2007, 9, 1987-1990.
DOI: 10.1021/ol0705907 (free Supporting Information)
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An intermolecular Ti(IV)-mediated cyclopropanation reaction has been used to synthesize substituted 2-phenylcyclopropylamines and constrained analogues of the neurotransmitters histamine and tryptamine. Many potent inhibitors of monoamine oxidase were made in 1 to 5 steps from readily available starting materials and have been shown to mimic hallucinogens.
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