title: Studies toward the synthesis of oximidines I and II.
abstract: The synthesis of compound 1, a precursor for the synthesis of the oximidine II core structure 2, is described. An undesired C8-C9 isomerization occurred during the intramolecular Castro-Stephens reaction leading to macrocyle 3. The thermodynamic driving force for this unexpected isomerization was established by DFT and MP2 calculations. [reaction: see text]
authors.affiliation: Department of Medicinal Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, KS 66045-7582, USA.
authors.forename: Torsten
authors.initials: T
authors.lastname: Haack
authors.forename: Serdar
authors.initials: S
authors.lastname: Kurtkaya
authors.forename: James P
authors.initials: JP
authors.lastname: Snyder
authors.forename: Gunda I
authors.initials: GI
authors.lastname: Georg
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D007783:Lactones / Q000138:chemical synthesis*; D008968:Molecular Conformation; D013237:Stereoisomerism; D013816:Thermodynamics
chemical_list: D000475:Alkenes; D007202:Indicators and Reagents; D007783:Lactones; C442268:oximidine I; C442267:oximidine II