Isolation and structure elucidation of new radical oxidation products of 5-hydroxy steroids |
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| Authors: | Khripach Vladimir A Zhabinskii Vladimir N Kuchto Anna I Zhiburtovich Yuliya Y Lyakhov Alexander S Govorova Alla A Groen Marinus B van der Louw Jaap de Groot Aede |
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| Institution: | Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, Kuprevich str., 5/2, 220141 Minsk, Belarus. khripach@iboch.bas-net.by |
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| Abstract: | Three new products have been isolated from the lead-tetraacetate version of the hypoiodite oxidation of 3beta,17beta-diacetoxy-5-hydroxy-5 alpha-androstane. Along with the expected 1(10)-unsaturated 5,10-seco steroidal 5-ketones, the fragmentation reaction gave two epimeric C-4 iodides. Their structural assignment was based on X-ray data of one of them ((4R,10S)-4-iodo-3beta,17beta-diacetoxy-5,10-secoandrostan-5-one). The third new product was found to be the 5 beta,6 beta-epoxide resulting from the dehydration of the tertiary alcohol followed by epoxidation of the intermediate Delta(5)-olefin. |
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| Keywords: | Secosteroids Radical oxidation Deiodination Transannular migration Dehydration |
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