123409-85-8Relevant articles and documents
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.
Diastereoselective synthesis of 3,5-trans-(+)-(3R,5R)-3-carbomethoxycarbapenam from 3-hydroxypyridine: Questioning the stereochemical assignment of the natural product
Tanaka, Hideyuki,Sakagami, Hideki,Ogasawara, Kunio
, p. 93 - 96 (2007/10/03)
An enantio- and diastereoselective synthesis of the methyl ester of 3,5-trans-(3R,5R)-carbapenam-3-carboxylic acid from 3-hydroxypyridine via (2R,5S)-trans-5-acetoxy-2-allylpiperidine has been achieved by employing the piperidine-pyrrolidine ring-contract