Author:
Khripach Vladimir A.,Zhabinskii Vladimir N.,Kotyatkina Anna I.,Fando Galina P.,Zhiburtovich Yuliya Y.,Lyakhov Alexander S.,Govorova Alla A.,Groen Marinus B.,Louw Jaap van der,Groot Aede de
Abstract
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.
Publisher
Institute of Organic Chemistry & Biochemistry
Cited by
15 articles.
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