title: Stereoselective route to the ezoaminuroic acid core of the ezomycins.
abstract: Starting from readily available (R)-glycidol, an efficient pathway to a strategically functionalized ezoaminuroic acid derivative of the antifungal ezomycins has been developed. A key transformation in the synthesis involves regio- and stereoselective conversion of the olefinic functionality of a 5,6-dihydropyran-2-one to the C-2, C-3 trans-1,2-amino alcohol moiety as present in ezoaminuroic acid.
authors.affiliation: Department of Medicinal Chemistry, 1251 Wescoe Hall Drive, University of Kansas, Lawrence, KS 66045, USA. adutta@ku.edu
authors.forename: Juhienah K
authors.initials: JK
authors.lastname: Khalaf
authors.forename: Apurba
authors.initials: A
authors.lastname: Datta
mesh_terms: D000617:Aminoglycosides / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D021241:Spectrometry, Mass, Electrospray Ionization; D013237:Stereoisomerism
chemical_list: D000617:Aminoglycosides; C039957:ezomycin