The development of a complementary pathway for the synthesis of aliskiren
文献类型：期刊论文
| 作者 | Li,Le-Le; Ding,Jin-Ying; Gao,Lian-Xun; Han,Fu-She |
| 刊名 | organic & biomolecular chemistry
 |
| 出版日期 | 2015 |
| 卷号 | 13期号:4页码:1133-1140 |
| 关键词 | RENIN INHIBITOR ALISKIREN ORALLY-ACTIVE INHIBITORS OLEFIN CROSS-METATHESIS CONVERGENT SYNTHESIS RUTHENIUM CATALYSTS OXIDATIVE CLEAVAGE POTENT CONVERSION ALCOHOLS KETONES |
| 通讯作者 | han,fs |
| 英文摘要 | the synthesis of aliskiren (1), a recently marketed drug for the treatment of hypertension, is presented. the focus of our synthetic effort is to develop an efficient pathway for the synthesis of (2s,7r,e)-2-isopropyl-7-(4-methoxy-3-(3-methoxypropoxy) benzyl)-n,n, 8-trimethylnon-4-enamide (2a), which has been used as the advanced intermediate toward aliskiren. after an extensive investigation of three different strategies designed to construct the e-olefin functionality in 2a by employing the olefin cross-metathesis, horner-wadsworth-emmons (hwe), and julia-type olefinations, we have established a new protocol for the synthesis of 2a with a substantially improved overall efficiency in terms of the yield (ca. 33%), and diastereo- and e/z-selectivity. the key transformations were the evans chiral auxiliary-aided asymmetric allylation for the synthesis of the appropriate chiral intermediates in excellent enantiomeric purity of higher than 97% ee and a modified julia-kocienski olefination for the highly selective construction of e-2a with up to 13.6 : 1 e/z ratio from the chiral intermediates. consequently, the results provide an appealing option for the synthesis of aliskiren. |
| 收录类别 | SCI |
| 语种 | 英语 |
| 公开日期 | 2016-05-31 |
| 源URL | [http://ir.ciac.jl.cn/handle/322003/67900]  |
| 专题 | 长春应用化学研究所_长春应用化学研究所知识产出_期刊论文 |
| 推荐引用方式 GB/T 7714 | Li,Le-Le,Ding,Jin-Ying,Gao,Lian-Xun,et al. The development of a complementary pathway for the synthesis of aliskiren[J]. organic & biomolecular chemistry,2015,13(4):1133-1140. |
| APA | Li,Le-Le,Ding,Jin-Ying,Gao,Lian-Xun,&Han,Fu-She.(2015).The development of a complementary pathway for the synthesis of aliskiren.organic & biomolecular chemistry,13(4),1133-1140. |
| MLA | Li,Le-Le,et al."The development of a complementary pathway for the synthesis of aliskiren".organic & biomolecular chemistry 13.4(2015):1133-1140. |
入库方式： OAI收割
来源：长春应用化学研究所
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