Studies toward the synthesis of oximidines I and II.
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]
Haack
Torsten
T
Department of Medicinal Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, KS 66045-7582, USA.
Kurtkaya
Serdar
S
Snyder
James P
JP
Georg
Gunda I
GI
D000475:Alkenes / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D007783:Lactones / Q000138:chemical synthesis*; D008968:Molecular Conformation; D013237:Stereoisomerism; D013816:Thermodynamics
D000475:Alkenes; D007202:Indicators and Reagents; D007783:Lactones; C442268:oximidine I; C442267:oximidine II