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Asymmetric Synthesis and Structure‐Activity Relationship of the Four Stereoisomers of the Antibiotic Amidinomycin Part 1: The Synthesis
Author(s) -
Sung SunYoung,
Frahm August Wilhelm
Publication year - 1996
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.19963290605
Subject(s) - reductive amination , chemistry , amination , stereochemistry , enantioselective synthesis , optically active , stereoisomerism , cis–trans isomerism , structural isomer , molecule , organic chemistry , catalysis
The natural amidinomycin (( 1 R , 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‐hydroxy‐iminocyclopentanecarboxylic acids ( 5a ) and lead to the trans ‐isomers of 14 .