The anionotropic rearrangement of a steroidal ethynyl-ethylenic alcohol
| Autor: | F. Sondheimer, A.D. Cross, J.C. Orr, M.L. Franco |
|---|---|
| Rok vydání: | 1964 |
| Předmět: |
inorganic chemicals
Pharmacology integumentary system organic chemicals Organic Chemistry Clinical Biochemistry Diol Alcohol Sulfuric acid Nuclear magnetic resonance spectroscopy Conjugated system Biochemistry Medicinal chemistry chemistry.chemical_compound Endocrinology chemistry Bromide polycyclic compounds Organic chemistry Hydroxydione Molecular Biology hormones hormone substitutes and hormone antagonists |
| Zdroj: | Steroids. 3:1-12 |
| ISSN: | 0039-128X |
| DOI: | 10.1016/0039-128x(64)90047-9 |
| Popis: | Reaction of 2-formyl-5α-androst-2-en-17β-ol (III) with ethynylmagnesium bromide yielded the ethynyl-ethylenic diol (IV). This diol was rearranged by means of sulfuric acid to the conjugated ethynyl-ethylenic diol (VIa), containing the 3-hydroxyl group in the α-configuration as evidenced by nuclear magnetic resonance spectroscopy. Other products obtained from (IV) by treatment with acid are the saturated hydroxydione (V), the methylfuran (VII) and the conjugated hydroxy-dienone (VIII). Some oxidation experiments carried out with the unconjugated diol (IV) and the conjugated diol (VIa) are described. |
| Databáze: | OpenAIRE |
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