The dirhodium(II) tetraacetate catalysed reaction of ethyl diazoacetate with 2,3-dihydropyrrole-2,2-dicarboxylate 5 afforded the useful 2-azabicyclo[3.1.0]hexane derivative 6. Its conversion into the proline-γ-acetic acid equivalent 9 as well as into the four isomers constituting the 4-(carboxymethyl)proline 13(16a–19a) whose absolute configuration was established by an alternative asymmetric synthesis of two of them is described. Preliminary data concerning the affinity of compounds 16a–19a for the NMDA site of the NMDA receptor complex are also reported.
Synthesis of All Four Diastereomers of 4-Carboxymethyl-proline, a Conformationally Constrained Analog of 2-Amino Adipic Acid
PELLICCIARI, Roberto;NATALINI, Benedetto;MARINOZZI, Maura;
1995
Abstract
The dirhodium(II) tetraacetate catalysed reaction of ethyl diazoacetate with 2,3-dihydropyrrole-2,2-dicarboxylate 5 afforded the useful 2-azabicyclo[3.1.0]hexane derivative 6. Its conversion into the proline-γ-acetic acid equivalent 9 as well as into the four isomers constituting the 4-(carboxymethyl)proline 13(16a–19a) whose absolute configuration was established by an alternative asymmetric synthesis of two of them is described. Preliminary data concerning the affinity of compounds 16a–19a for the NMDA site of the NMDA receptor complex are also reported.File in questo prodotto:
Non ci sono file associati a questo prodotto.
I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
