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.
MeSH terms
-
Amino Acids, Cyclic / chemical synthesis*
-
Amino Acids, Cyclic / chemistry
-
Dicarboxylic Acids / chemical synthesis*
-
Dicarboxylic Acids / chemistry
-
Hexanes / chemistry*
-
Humans
-
Molecular Structure
-
Receptors, Metabotropic Glutamate / agonists
-
Receptors, Metabotropic Glutamate / physiology
-
Stereoisomerism
Substances
-
2-aminobicyclo(3.1.0)hexane-2,6-dicarboxylate
-
Amino Acids, Cyclic
-
Dicarboxylic Acids
-
Hexanes
-
Receptors, Metabotropic Glutamate
-
n-hexane