Enantiopure synthesis of all four stereoisomers of carbapenam-3-carboxylic acid methyl ester.
The retro-Dieckmann reaction has been used as a stereodivergent synthetic tool on N-Boc-7-azabicyclo[2.2.1]heptan-2-one-1-carboxylic acid methyl ester to obtain enantiopure trans- and cis-5-(carboxymethyl)pyrrolidine-2-carboxylic acid methyl esters. These disubstituted pyrrolidines have been used as starting materials to develop concise and straightforward syntheses of all four stereoisomers of carbapenam-3-carboxylic acid methyl esters. In this way, we have confirmed unequivocally the stereochemistry of two carbapenams isolated from strains of Serratia and Erwinia species.
Avenoza
Alberto
A
Departamento de Química, Universidad de La Rioja, Grupo de Síntesis Química de La Rioja, U.A.-C.S.I.C., E-26006 Logroño, Spain. alberto.avenoza@dq.unirioja.es
Barriobero
José I
JI
Busto
Jesús H
JH
Peregrina
Jesús M
JM
D000900:Anti-Bacterial Agents / Q000032:analysis / Q000138:chemical synthesis*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D004885:Erwinia / Q000737:chemistry; D007202:Indicators and Reagents; D007769:Lactams / Q000138:chemical synthesis*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D012705:Serratia / Q000737:chemistry; D013237:Stereoisomerism
D000900:Anti-Bacterial Agents; D007202:Indicators and Reagents; D007769:Lactams; C057567:carbapenam-3-carboxylic acid