title: Enantioselective synthesis of the excitatory amino acid (1S,3R)-1-aminocyclopentane-1,3-dicarboxylic acid.
abstract: An enantioselective synthesis of the alpha,alpha-dialkyl-alpha-amino acid (1S,3R)-ACPD has been achieved using an alkylidene carbene 1,5-CH insertion reaction as a key step. The ketone cyclization precursor was synthesized from Garner's aldehyde in high yield via a Wittig homologation and subsequent catalytic hydrogenation. Treatment of the ketone with 1.2 equiv of lithio(trimethylsilyl)diazomethane in THF resulted in the formation of the corresponding cyclopentene-containing CH-insertion product in 62-69% yield in high enantiomeric excess. Subsequent functional group manipulation allowed the synthesis of the amino acid (1S,3R)-ACPD to be completed.
authors.affiliation: The School of Chemistry, University of Nottingham, University Park, UK.
authors.forename: Daniel M
authors.initials: DM
authors.lastname: Bradley
authors.forename: Renameditswe
authors.initials: R
authors.lastname: Mapitse
authors.forename: Nicholas M
authors.initials: NM
authors.lastname: Thomson
authors.forename: Christopher J
authors.initials: CJ
authors.lastname: Hayes
mesh_terms: D003515:Cycloleucine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry*; D018846:Excitatory Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D018846:Excitatory Amino Acids; D003515:Cycloleucine; C036361:1-amino-1,3-dicarboxycyclopentane