Enantiopure Synthesis of All Four Stereoisomers of Carbapenam-3-carboxylic Acid Methyl Ester
- Avenoza, A. 1
- Barriobero, J.I. 1
- Busto, J.H. 1
- Peregrina, J.M. 1
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1
Universidad de La Rioja
info
ISSN: 0022-3263
Any de publicació: 2003
Volum: 68
Número: 7
Pàgines: 2889-2894
Tipus: Article
Altres publicacions en: Journal of Organic Chemistry
Resum
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.