180323-35-7Relevant academic research and scientific papers
Asymmetric synthesis and structure-activity relationship of the four stereoisomers of the antibiotic amidinomycin part 1: The synthesis
Sung, Sun-Young,Frahm, August Wilhelm
, p. 291 - 300 (1996)
The natural amidinomycin ((1R, 3S)-14) and its three stereoisomers are synthesized from homochiral 3-oxocyclopentanecarboxylic acids (1a) by asymmetric methods, which are based on an asymmetric reductive amination to produce methyl cis-N-(1-phenylethyl)-3-aminocyclo-pentanecarboxylates (3b) via optically active methyl N-(1-phenylethyl)-3-iminocyclopentane- carboxylates (2b) for the cis-isomers of 14. Optically pure trans-3- aminocyclopentane-carboxylic acids (4a) are obtained from the homochiral keto acids 1a via asymmetric reductive amination of 3- hydroxyiminocyclopentanecarboxylic acids (5a) and lead to the trans-isomers of 14.
