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

Autor: Loránd Kiss, Enikő Forró, György Orsy, Renáta Ábrahámi, Ferenc Fülöp
Jazyk: angličtina
Rok vydání: 2015
Předmět:
Zdroj: Molecules, Vol 20, Iss 12, Pp 21094-21102 (2015)
Druh dokumentu: article
ISSN: 1420-3049
DOI: 10.3390/molecules201219749
Popis: 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.
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