523988-38-7Relevant academic research and scientific papers
Convenient syntheses of (3S,5S)-carbapenam-3-carboxylates and their biosynthetic relevance
Bycroft, Barrie W.,Chhabra, Siri Ram,Kellam, Barrie,Smith, Paul
, p. 973 - 976 (2007/10/03)
Starting from readily available glutamate derivatives, facile stereoselective syntheses of (3S,5S)-carbapenam-3-carboxylates have been developed. Their significance in confirming the absolute configuration of the natural material is discussed.
Enantiopure synthesis of all four stereoisomers of carbapenam-3-carboxylic acid methyl ester
Avenoza, Alberto,Barriobero, Jose I.,Busto, Jesus H.,Peregrina, Jesus M.
, p. 2889 - 2894 (2007/10/03)
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.
