Synthesis of new optically active 2-pyrrolidinones.
A new class of optically active 2-pyrrolidinones was synthesized, starting from S-pyroglutamic acid, a well known natural chiral synthon. The synthetic design followed led to the insertion of various substituents at positions 1 and 5 of the 2-pyrrolidinone ring, including the imidazole moiety. Some of them possess two or three stereogenic centers, the configuration of which was retained under the mild conditions used. The new compounds also carry an imidazole moiety, which, along with the 2-pyrrolidinone template, may prove pivotal to several biological processes.
Laboratory of Organic Chemistry, Department of Chemistry, University of Athens, Panepistimiopolis, Athens, Greece. pminakak@chem.uoa.gr
Panagiota
P
Moutevelis-Minakakis
Eleni
E
Papavassilopoulou
Thomas
T
Mavromoustakos
D006639:Histidine / Q000378:metabolism; D007093:Imidazoles / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D011760:Pyrrolidinones / Q000138:chemical synthesis*; D011761:Pyrrolidonecarboxylic Acid / Q000378:metabolism; D012694:Serine / Q000378:metabolism
D007093:Imidazoles; D011760:Pyrrolidinones; D012694:Serine; D006639:Histidine; C029899:imidazole; D011761:Pyrrolidonecarboxylic Acid