title: Synthesis of enantiopure cyclopropyl esters from (-)-levoglucosenone.
abstract: The biorenewable chiral synthon (-)-levoglucosenone has been converted to enantiopure cyclopropyl esters using the base-promoted carbocyclisation of 4,5-epoxyvalerates. This protocol was applied to the enantiospecific synthesis of the GABAc receptor agonist (1R,2R)-trans-2-aminomethylcyclopropanecarboxylic acid ((-)-TAMP) and its enantiomer. The process was also extended to generate 1,1,2- and 1,2,3-trisubstituted cyclopropanes resulting in a formal synthesis of the selective glutamate receptor antagonist PCCG-4.
authors.affiliation: School of Science and Technology, University of New England, Armidale, NSW, Australia2351. ben.greatrex@une.edu.au.
authors.forename: Kieran P
authors.initials: KP
authors.lastname: Stockton
authors.forename: Ben W
authors.initials: BW
authors.lastname: Greatrex
mesh_terms: D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry*; D003521:Cyclopropanes / Q000138:chemical synthesis* / Q000737:chemistry; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry; D005947:Glucose / Q000031:analogs & derivatives* / Q000737:chemistry; D008968:Molecular Conformation
chemical_list: D019086:Bridged Bicyclo Compounds, Heterocyclic; D003521:Cyclopropanes; D004952:Esters; C512757:1,6-anhydro-3,4-dideoxyhex-3-enopyran-2-ulose; D005947:Glucose