Stereo- and Regiocontrolled Syntheses of Exomethylenic Cyclohexane β-Amino Acid Derivatives.
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.
['Kiss|Loránd|L|', 'Forró|Enikő|E|', 'Orsy|György|G|', 'Ábrahámi|Renáta|R|', 'Fülöp|Ferenc|F|']
D000596:Amino Acids D000935:Antifungal Agents D003510:Cyclohexanes D003515:Cycloleucine D005658:Fungi D006900:Hydroxylation D015394:Molecular Structure D010084:Oxidation-Reduction D047090:beta-Lactams
icofungipen selectivity hydroxylation Wittig reaction amino acids