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Open AccessArticle

Stereo- and Regiocontrolled Syntheses of Exomethylenic Cyclohexane β-Amino Acid Derivatives

1
Institute of Pharmaceutical Chemistry, University of Szeged, H-6720 Szeged, Hungary
2
Stereochemistry Research Group of the Hungarian Academy of Sciences, University of Szeged, H-6720 Szeged, Eötvös 6, Hungary
*
Author to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Molecules 2015, 20(12), 21094-21102; https://doi.org/10.3390/molecules201219749
Received: 15 October 2015 / Revised: 12 November 2015 / Accepted: 19 November 2015 / Published: 27 November 2015
(This article belongs to the Section Organic Chemistry)
Cyclohexane analogues of the antifungal icofungipen [(1R,2S)-2-amino-4-methylenecyclopentanecarboxylic acid] were selectively synthesized from unsaturated bicyclic β-lactams by transformation of the ring olefinic bond through three different regio- and stereocontrolled hydroxylation techniques, followed by hydroxy group oxidation and oxo-methylene interconversion with a phosphorane. Starting from an enantiomerically pure bicyclic β-lactam obtained by enzymatic resolution of the racemic compound, an enantiodivergent procedure led to the preparation of both dextro- and levorotatory cyclohexane analogues of icofungipen. View Full-Text
Keywords: amino acids; selectivity; hydroxylation; Wittig reaction; icofungipen amino acids; selectivity; hydroxylation; Wittig reaction; icofungipen
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MDPI and ACS Style

Kiss, L.; Forró, E.; Orsy, G.; Ábrahámi, R.; Fülöp, F. Stereo- and Regiocontrolled Syntheses of Exomethylenic Cyclohexane β-Amino Acid Derivatives. Molecules 2015, 20, 21094-21102.

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