| A new approach for the asymmetric syntheses of 2-epi-deoxoprosopinine and azasugar derivatives | |
| Bang-Guo Wei ; Jie Chen ; Pei-Qiang Huang | |
| 2005-10-24 | |
| 关键词 | Piperidine Alkaloid Hydroxymethylation Diastereoselective reaction Regioselective reaction Building block |
| 英文摘要 | A new approach to 2-epi-deoxoprosopinine 11, 1-deoxygulonojirimycin 7, and l-gulono-1,5-lactam 9 was described. The C-2 hydroxymethyl group was introduced regioselectively using SmI2 mediated coupling of (S)-3-silyloxyglutarimide 13b with either chloromethyl benzyl ether 16a or the Beau–Skrydstrup reagent 16b, followed by debenzylation and highly cis-diastereoselective reductive deoxygenation. Adoption of the Savoi's chemoselective ring-opening alkylation method allowed a highly diastereoselective introduction of the lipid side chain of 2-epi-deoxoprosopinine 11 in a straightforward manner. Dehydration followed by highly trans-diastereoselective dihydroxylation led to polyoxygenated lactam derivative 27 as a key intermediate for the syntheses of 7 and 9.; the NSF of China (20272048; 203900505) and the Ministry of Education (Key Project 104201). |
| 语种 | 英语 |
| 出版者 | Elsevier Inc. |
| 内容类型 | 期刊论文 |
| 源URL | [http://dspace.xmu.edu.cn/handle/2288/2805]  |
| 专题 | 化学化工－已发表论文 |
| 推荐引用方式 GB/T 7714 | Bang-Guo Wei,Jie Chen,Pei-Qiang Huang. A new approach for the asymmetric syntheses of 2-epi-deoxoprosopinine and azasugar derivatives[J],2005. |
| APA | Bang-Guo Wei,Jie Chen,&Pei-Qiang Huang.(2005).A new approach for the asymmetric syntheses of 2-epi-deoxoprosopinine and azasugar derivatives.. |
| MLA | Bang-Guo Wei,et al."A new approach for the asymmetric syntheses of 2-epi-deoxoprosopinine and azasugar derivatives".(2005). |
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