Collection of Czechoslovak Chemical Communications · 2001 · 12 citations · 9 references
Life SciencesBiochemistryChemistryHormone BiochemistryRedox BiochemistrySteroid BiochemistrySteroid Hormone BiochemistrySteroid StructureFree Radical OxidationOxidationSteroid Oxidation StatesX-ray Spectral Analysis
The radical oxidation of 14α-hydroxy steroids with various functional groups at C-17 was studied. Lead tetraacetate and ceric ammonium nitrate were used as oxidizing agents. It was shown that reactions of this type afforded complex mixtures of compounds. However, the radical oxidation of 14α-hydroxy-17-oxo steroid (lead tetraacetate version of the hypoiodite reaction) proceeded smoothly with formation of the 13,14-secosteroid in up to 85% yield. The structure and conformation of the formed 13α-iodo-3α,5-cyclo-13,14-seco-5α-androst-5-ene-14,17-dione was determined by X-ray analysis.
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