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

Kiss, Loránd and Forró, Enikő and Orsy, György and Ábrahámi, Renáta and Fülöp, Ferenc (2015) Stereo- and Regiocontrolled Syntheses of Exomethylenic Cyclohexane Beta-Amino Acid Derivatives. MOLECULES. pp. 21094-21102. ISSN 1420-3049

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Abstract

Cyclohexane analogues of the antifungal icofungipen [(1R,2S)-2-amino-4-methylenecy clopentanecarboxylic acid] were selectively synthesized from unsaturated bicyclic beta-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 beta-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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