Radical oxidation of 17-functionalized 14alpha-hydroxy steroids
| Autor: | Yuliya Y. Zhiburtovich, Alla A. Govorova, Alexander S. Lyakhov, Galina P. Fando, Anna I. Kotyatkina, Vladimir N. Zhabinskii, Jaap van der Louw, Vladimir A. Khripach, Aede de Groot, Marinus B. Groen |
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| Jazyk: | angličtina |
| Rok vydání: | 2001 |
| Předmět: |
Chemistry
Lead tetraacetate medicine.medical_treatment Organic Chemistry Radical oxidation General Chemistry Medicinal chemistry Organische Chemie Steroid chemistry.chemical_compound Secosteroids Fragmentation Oxidizing agent medicine Conformation analysis Steroids Ceric ammonium nitrate Radical oxidations |
| Zdroj: | Collection of Czechoslovak Chemical Communications, 66, 1764-1776 Collection of Czechoslovak Chemical Communications 66 (2001) |
| ISSN: | 0010-0765 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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