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Molecules 2015, 20(12), 21094-21102; doi:10.3390/molecules201219749

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
Received: 15 October 2015 / Revised: 12 November 2015 / Accepted: 19 November 2015 / Published: 27 November 2015
(This article belongs to the Section Organic Synthesis)
View Full-Text   |   Download PDF [2855 KB, uploaded 27 November 2015]   |  

Abstract

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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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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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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