title: Improved synthesis of C4α- and C4β-methyl analogues of 2-aminobicyclo[3.1.0]hexane-2,6-dicarboxylate.
abstract: An efficient and divergent synthesis of C4α- and C4β-methyl-substituted analogues of 2-aminobicyclo[3.1.0]hexane 2,6-dicarboxylate, which are important tools in the study of metabotropic glutamate receptor function, has been achieved. By taking advantage of an unanticipated facial selectivity of the bicyclo[3.1.0]hexane ring system, either the C4α- or C4β-methyl substituent was introduced in a highly stereoselective and high-yielding manner.
authors.affiliation: Discovery Chemistry Research and Technologies, Eli Lilly and Company, Indianapolis, Indiana 46285, USA. sshenry@lilly.com
authors.forename: Steven S
authors.initials: SS
authors.lastname: Henry
authors.forename: Molly D
authors.initials: MD
authors.lastname: Brady
authors.forename: Dana L T
authors.initials: DL
authors.lastname: Laird
authors.forename: J Craig
authors.initials: JC
authors.lastname: Ruble
authors.forename: David L
authors.initials: DL
authors.lastname: Varie
authors.forename: James A
authors.initials: JA
authors.lastname: Monn
mesh_terms: D000598:Amino Acids, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D003998:Dicarboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D006586:Hexanes / Q000737:chemistry*; D006801:Humans; D015394:Molecular Structure; D018094:Receptors, Metabotropic Glutamate / Q000819:agonists / Q000502:physiology; D013237:Stereoisomerism
chemical_list: C574391:2-aminobicyclo(3.1.0)hexane-2,6-dicarboxylate; D000598:Amino Acids, Cyclic; D003998:Dicarboxylic Acids; D006586:Hexanes; D018094:Receptors, Metabotropic Glutamate; C026385:n-hexane