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Issue 11, 1994
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Asymmetric synthesis of (–)-(1R,2S)-cispentacin and related cis- and trans-2-amino cyclopentane- and cyclohexane-1-carboxylic acids

Abstract

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.

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Article type: Paper
DOI: 10.1039/P19940001411
Citation: J. Chem. Soc., Perkin Trans. 1, 1994,0, 1411-1415
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    Asymmetric synthesis of (–)-(1R,2S)-cispentacin and related cis- and trans-2-amino cyclopentane- and cyclohexane-1-carboxylic acids

    S. G. Davies, O. Ichihara, I. Lenoir and I. A. S. Walters, J. Chem. Soc., Perkin Trans. 1, 1994, 0, 1411
    DOI: 10.1039/P19940001411

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