Stereo- and Regiocontrolled Syntheses of Exomethylenic Cyclohexane β-Amino Acid DerivativesReportar como inadecuado




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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

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





Autor: Loránd Kiss 1, Enikő Forró 1, György Orsy 1, Renáta Ábrahámi 1 and Ferenc Fülöp 1,2,*

Fuente: http://mdpi.com/



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