title: Stereoselective synthesis of (1S,3R)-1-aminocyclopentane-1,3-dicarboxylic acid via C-H insertion of alkylidenecarbene.
abstract: (1S,3R)-1-Aminocyclopentane-1,3-dicarboxylic acid (ACPD), a potent agonist of metabotropic glutamate receptors, was synthesized from L-serine. The chiral quaternary center was constructed by C-H insertion of the alkylidenecarbene, this being generated by the reaction between lithiotrimethylsilyldiazomethane and the corresponding ketone.
authors.affiliation: Department of Biological Chemistry, Faculty of Science, Okayama University of Science, Japan. sohira@dbc.ous.ac.jp
authors.forename: Susumu
authors.initials: S
authors.lastname: Ohira
authors.forename: Megumi
authors.initials: M
authors.lastname: Akiyama
authors.forename: Kumiko
authors.initials: K
authors.lastname: Kamihara
authors.forename: Yuichi
authors.initials: Y
authors.lastname: Isoda
authors.forename: Atsuhito
authors.initials: A
authors.lastname: Kuboki
mesh_terms: D003515:Cycloleucine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D003998:Dicarboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D007202:Indicators and Reagents; D007659:Ketones / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D018094:Receptors, Metabotropic Glutamate / Q000037:antagonists & inhibitors*; D013237:Stereoisomerism
chemical_list: D003998:Dicarboxylic Acids; D007202:Indicators and Reagents; D007659:Ketones; D018094:Receptors, Metabotropic Glutamate; D003515:Cycloleucine; C036361:1-amino-1,3-dicarboxycyclopentane