title: Stereo- and Regiocontrolled Syntheses of Exomethylenic Cyclohexane β-Amino Acid Derivatives.
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.
authors.affiliation: Institute of Pharmaceutical Chemistry, University of Szeged, H-6720 Szeged, Hungary. kiss.lorand@pharm.u-szeged.hu.
authors.forename: Loránd
authors.initials: L
authors.lastname: Kiss
authors.affiliation: Institute of Pharmaceutical Chemistry, University of Szeged, H-6720 Szeged, Hungary. forro.eniko@pharm.u-szeged.hu.
authors.forename: Enikő
authors.initials: E
authors.lastname: Forró
authors.affiliation: Institute of Pharmaceutical Chemistry, University of Szeged, H-6720 Szeged, Hungary. Orsy.gyorgy@pharm.u-szeged.hu.
authors.forename: György
authors.initials: G
authors.lastname: Orsy
authors.affiliation: Institute of Pharmaceutical Chemistry, University of Szeged, H-6720 Szeged, Hungary. abrahami.renata@pharm.u-szeged.hu.
authors.forename: Renáta
authors.initials: R
authors.lastname: Ábrahámi
authors.affiliation: Institute of Pharmaceutical Chemistry, University of Szeged, H-6720 Szeged, Hungary. fulop@pharm.u-szeged.hu.|Stereochemistry Research Group of the Hungarian Academy of Sciences, University of Szeged, H-6720 Szeged, Eötvös 6, Hungary. fulop@pharm.u-szeged.hu.
authors.forename: Ferenc
authors.initials: F
authors.lastname: Fülöp
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D003510:Cyclohexanes / Q000737:chemistry*; D003515:Cycloleucine / Q000031:analogs & derivatives; D005658:Fungi / Q000187:drug effects*; D006900:Hydroxylation; D015394:Molecular Structure; D010084:Oxidation-Reduction; D047090:beta-Lactams / Q000737:chemistry*
chemical_list: D000596:Amino Acids; D000935:Antifungal Agents; D003510:Cyclohexanes; D047090:beta-Lactams; D003515:Cycloleucine; C506365:Cyclohexane; C114614:2-amino-4-methylenecyclopentane-1-carboxylic acid
keywords: Wittig reaction; amino acids; hydroxylation; icofungipen; selectivity