Asymmetric synthesis of (–)-(1R,2S)-cispentacin and related cis- and trans-2-amino cyclopentane- and cyclohexane-1-carboxylic acids
- 1 January 1994
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 11,p. 1411-1415
- https://doi.org/10.1039/p19940001411
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.Keywords
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