A Synthesis of (-)-cis-2-Aminomethylcyclopropanecarboxylic Acid [(-)-CAMP]

Abstract

An enantioselective synthesis of (-)-cis-2-aminomethylcyclopropanecarboxylic acid [(-)-CAMP] has been achieved in 2.5% total yield over ten steps starting from 2-furaldehyde. The synthesis features diastereoselective cyclopropane formation via diazene, followed by oxime formation and the reduction, for construction of the γ-aminobutyric acid (GABA) motif.

Studies on lipase-catalyzed asymmetric synthesis of (S)-(hydroxymethyl)glutamic acid (HMG)

“…We have been also interested in the synthesis of the neuronally active compounds, by the divergent route amenable to the structural analogs to discover novel compounds (Chiba et al 2015 ; Juknaitė et al 2013 ; Oikawa et al 2013 ; Sakai et al 2014 ; Sugeno et al 2014 ; Tanaka et al 2015 ). Here, we report our synthetic study using lipase-mediated esterification of prochiral acyclic 1,3-diol as the key step.…”