Efficient Synthesis of Octandrenolone and Related Dipyranoacetophenones
| Autor: | Muyard F, Vaquette J, François Tillequin, Bevalot F, Pernin R |
|---|---|
| Rok vydání: | 2000 |
| Předmět: |
Ketone
Spectrophotometry Infrared Iodide Diol Pharmaceutical Science Methylation Plant Roots Chemical synthesis Mass Spectrometry Analytical Chemistry Catalysis chemistry.chemical_compound Hydrolysis Drug Discovery Organic chemistry Phenols Pharmacology chemistry.chemical_classification Chemistry Organic Chemistry Acetophenones Plants Complementary and alternative medicine Yield (chemistry) Molecular Medicine Indicators and Reagents Spectrophotometry Ultraviolet Chromatography Thin Layer Oxidation-Reduction |
| Zdroj: | Journal of Natural Products. 63:245-247 |
| ISSN: | 1520-6025 0163-3864 |
| DOI: | 10.1021/np9902845 |
| Popis: | Octandrenolone (1) was prepared in high yield by condensation of 2', 4',6'-trihydroxyacetophenone with 3-chloro-3-methylbut-1-yne in the presence of a catalytic amount of copper(I) iodide. Methylation of 1 afforded O-methyloctandrenolone (2). Oxidation of 2 with m-chloroperoxybenzoic acid followed by hydrolysis gave the racemic trans-(+)-1-(9,10-dihydro-9,10-dihydroxy-5-methoxy-2,2,8, 8-tetramethyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-6-yl)ethanone (3), which confirmed the structure of the natural product previously isolated from Melicope erromangensis. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|