Asymmetric synthesis of (-)-(1R,2S)-cispentacin and related cis- and trans-2-amino cyclopentane- and cyclohexane-1-carboxylic acids
Davies SG., Ichihara O., Lenoir I., Walters LAS.
The antifungal antibiotic (-)-(1R,2S)-2-aminocyclopentane-1-carboxylic acid (cispentacin)8 and its cyclohexane homologue 14 have been prepared utilizing the highly stereoselective conjugate addition of homochiral lithium N-benzyl-N-α-methylbenzylamide 5. The corresponding trans-β-amino acids 10 and 16 were also prepared via the selective epimerization of the cis-β-amino ester conjugate addition products. © 1994 by the Royal Society of Chemistry. All Rights Reserved.