Enantiopure synthesis of all four stereoisomers of carbapenam-3-carboxylic acid methyl ester

J Org Chem. 2003 Apr 4;68(7):2889-94. doi: 10.1021/jo026804+.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / analysis
  • Anti-Bacterial Agents / chemical synthesis*
  • Catalysis
  • Combinatorial Chemistry Techniques*
  • Erwinia / chemistry
  • Indicators and Reagents
  • Lactams / chemical synthesis*
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Serratia / chemistry
  • Stereoisomerism

Substances

  • Anti-Bacterial Agents
  • Indicators and Reagents
  • Lactams
  • carbapenam-3-carboxylic acid