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Synthesis of (25R)-26-hydroxy-15-ketosterols☆
| Content Provider | Semantic Scholar |
|---|---|
| Author | Kim, Hong-Seok Kim, Dong-Il |
| Copyright Year | 1999 |
| Abstract | (25R)-3beta,26-Dihydroxy-5alpha-cholest-8(14)-en-15-one (1) and (25R)-3beta,26-dihydroxy-5alpha,14beta-cholest-16-en-1 5-one (2) were synthesized from (25R)-3beta,26-dibenzoyloxy-5alpha,14alpha-chole st-16-ene (4). Oxidation of 4 with CrO3-3,5-dimethylpyrazole at -20 degrees C gave (25R)-3beta,26-dibenzoyloxy-5alpha,14alpha-chole st-16-en-15-one (5) along with (25R)-3beta,26-dibenzoyloxy-5alpha-cholest-16alpha+ ++,17alpha-epoxide (6). Oxidation of 5 with selenium dioxide afforded (25R)-3beta,26-dibenzoyloxy-5alpha-cholest-8(14),16-++ +dien-15-one (7) and (25R)-3beta,26-dibenzoyloxy-5alpha,14beta-choles t-16-en-15-one (8). Selective hydrogenation of 7 followed by hydrolysis in alcoholic potassium hydroxide yielded (25R)-3beta,26-dihydroxy-5alpha-cholest-8(14)-en-15-one (1). Hydrolysis of 5 and 8 in alcoholic potassium hydroxide provided (25R)-3beta,26-dihydroxy-5alpha,14beta-cholest-16-en-1 5-one (2). |
| Starting Page | 844 |
| Ending Page | 848 |
| Page Count | 5 |
| File Format | PDF HTM / HTML |
| DOI | 10.1016/S0039-128X(99)00065-3 |
| PubMed reference number | 10576219 |
| Journal | Medline |
| Volume Number | 64 |
| Alternate Webpage(s) | https://api.elsevier.com/content/article/pii/S0039128X99000653 |
| Alternate Webpage(s) | https://www.sciencedirect.com/science/article/pii/S0039128X99000653?dgcid=api_sd_search-api-endpoint |
| Alternate Webpage(s) | https://doi.org/10.1016/S0039-128X%2899%2900065-3 |
| Journal | Steroids |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |
