Study on steroidal oximinoethers: synthesis and stereostructure by NMR spectroscopy.
The condensation of O-substituted hydroxylamines with conjugated 3-oxo-4-en steroids results in a mixture of syn-anti configurations. Syn-anti ratios are influenced by sterical hindrance between the oximino substituents (e.g. O-benzyl) and the steroidal skeleton. Stereostructures and isomeric ratios were proved by detailed 1H and 13C NMR studies and also by using 2D-COSY, 2D-HSC, DEPT, 2D-COLOC and DNOE measurements.
Department of General and Inorganic Chemistry, Loránd Eötvös University, Budapest, Hungary. sohar@para.chem.elte.hu
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P
Sohár
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A
Bodor
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R
Schwartz
D004987:Ethers / Q000737:chemistry*; D006898:Hydroxylamines / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D015394:Molecular Structure; D009466:Neuromuscular Blocking Agents / Q000138:chemical synthesis; D010091:Oximes / Q000737:chemistry*; D013237:Stereoisomerism; D013256:Steroids / Q000138:chemical synthesis* / Q000737:chemistry
D004987:Ethers; D006898:Hydroxylamines; D009466:Neuromuscular Blocking Agents; D010091:Oximes; D013256:Steroids