Synthesis of 16 alpha-hydroxyandrost-4-ene-3,17,19-trione and 3 beta, 16 alpha-dihydroxyandrost-5-ene-17,19-dione; potential intermediates of estriol biosynthesis
| Autor: | Mitsuteru Numazawa, Masao Nagaoka, Kumiko Hoshi, Tomomi Konno |
|---|---|
| Rok vydání: | 1990 |
| Předmět: |
chemistry.chemical_classification
Jones oxidation Chemical Phenomena Estriol Androstenedione Ether General Chemistry General Medicine Aldehyde Silyl ether chemistry.chemical_compound Chemistry chemistry Reagent Drug Discovery Androstenediols Organic chemistry Pyridinium Sulfhydryl Compounds Enone Ene reaction |
| Zdroj: | Chemicalpharmaceutical bulletin. 38(7) |
| ISSN: | 0009-2363 |
| Popis: | 16 alpha-Hydroxyandrost-4-ene-3,17,19-trione (10) was synthesized from the 16 alpha-hydroxy-6 beta,19-epoxy-17-one 3 via protection of the 16 alpha-hydroxy function as its tert-butyldimethylsilyl ether or acetate. Reductive cleavage of the epoxy ring of the silyl ether 4 or the acetate 5 with zinc dust gave the 19-alcohol 6 or 7, which was treated with pyridinium dichromate or Jones reagent, respectively, and then hydrolyzed with diluted sulfuric acid, yielding the desired steroid 10. 3 beta,16 alpha-Dihydroxyandrost-5-ene-17,19-dione (14) was also synthesized from 5 alpha-bromo-3 beta,16 alpha-diacetoxy-6 beta, 19-epoxyandrostan-17-one (11) through the intermediates 12 and 13 with the 3 beta- and 16 alpha-hydroxy functions protected as their acetates in a reaction sequence similar to that above. |
| Databáze: | OpenAIRE |
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