Enantiopure Synthesis of All Four Stereoisomers of Carbapenam-3-carboxylic Acid Methyl Ester

  1. Avenoza, A. 1
  2. Barriobero, J.I. 1
  3. Busto, J.H. 1
  4. Peregrina, J.M. 1
  1. 1 Universidad de La Rioja
    info

    Universidad de La Rioja

    Logroño, España

    ROR https://ror.org/0553yr311

Revista:
Journal of Organic Chemistry

ISSN: 0022-3263

Año de publicación: 2003

Volumen: 68

Número: 7

Páginas: 2889-2894

Tipo: Artículo

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DOI: 10.1021/JO026804+ PMID: 12662066 SCOPUS: 2-s2.0-0037419340 WoS: WOS:000181953700046 GOOGLE SCHOLAR

Otras publicaciones en: Journal of Organic Chemistry

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Resumen

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.