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Stereoselective reduction of C-2 substituted steroid C-3 ketones with lithium tris-(R,S-1,2-dimethylpropyl)-borohydride and sodium borohydride
| Content Provider | Semantic Scholar |
|---|---|
| Author | Templeton, John F. Kumar, V. P. Sashi Gupta, Ram K. Friesen, Anne M. |
| Copyright Year | 1986 |
| Abstract | The effect of C-2 substitution on the stereoselective reduction of steroid C-3 ketones with lithium tris-(R,S-1,2-dimethylpropyl)-borohydride and sodium borohydride was investigated. The C-2 mono- and di-substituted chloro and methyl derivatives were predominantly reduced to one of the epimeric alcohols. The 2 alpha-chloro and 2 alpha-methyl derivatives of 17 beta-acetoxy-5 alpha-androstan-3-one undergo stereoselective reduction with lithium tris-(R,S-1,2-dimethylpropyl)-borohydride to the axial (3 alpha) alcohol as observed in the unsubstituted compound, whereas sodium borohydride gives predominantly the equatorial (3 beta) alcohol. The 2 beta-chloro, 2 beta-methyl, 2,2-dichloro, and 2,2-dimethyl derivatives are reduced predominantly to the equatorial (3 beta) alcohol by both reagents. |
| Starting Page | 339 |
| Ending Page | 346 |
| Page Count | 8 |
| File Format | PDF HTM / HTML |
| DOI | 10.1016/0039-128X(86)90020-6 |
| PubMed reference number | 3445286 |
| Journal | Medline |
| Volume Number | 48 |
| Alternate Webpage(s) | https://api.elsevier.com/content/article/pii/0039128X86900206 |
| Alternate Webpage(s) | https://www.sciencedirect.com/science/article/pii/0039128X86900206?dgcid=api_sd_search-api-endpoint |
| Alternate Webpage(s) | https://doi.org/10.1016/0039-128X%2886%2990020-6 |
| Journal | Steroids |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |
