| 群柱虫内酯官能团化的C2-C10片段的立体选择性合成 |
| |
| 引用本文： | 周佐中,a,b 索栋,b 杨震宇,b 陈琳,a 胡泰山,b 姚祝军,b.群柱虫内酯官能团化的C2-C10片段的立体选择性合成[J].中国化学,2009,27(1):135-140. |
| |
| 作者姓名： | 周佐中 a b 索栋 b 杨震宇 b 陈琳 a 胡泰山 b 姚祝军 b |
| |
| 作者单位： | a云南民族大学化学与生物技术学院，昆明，云南650031； ;b中国科学院上海有机化学研究所生命有机化学国家重点实验室，上海200032 ; |
| |
| 摘 要： | 本文以廉价的消旋甲基戊二酸酐为起始原料，完成了具有抗肿瘤活性的海洋天然产物群柱虫内酯（Clavulactone）官能团化的C2-C10片段的立体选择性合成。使用的关键方法包括不对称去对称化获得光学纯手性孤立甲基，和RCM方法构建顺式烯烃。该片段的获得为群柱虫内酯的全合成提供了基础。
|
| 关 键 词： | 群蛀虫内酯 朵蕾烷二萜 去对称化 关环复分解反应 立体选择性 |
| 收稿时间： | 2008-8-4 |
| 修稿时间： | 2008-10-13 |
Stereoselective Synthesis of the Functionalized C2–C10 Fragment of Clavulactone |
| |
| Zuozhong ZHOU,Dong SUO,Zhenyu YANG,Lin CHEN,Taishan HU,Zhujun YAO.Stereoselective Synthesis of the Functionalized C2–C10 Fragment of Clavulactone[J].Chinese Journal of Chemistry,2009,27(1):135-140. |
| |
| Authors: | Zuozhong ZHOU Dong SUO Zhenyu YANG Lin CHEN Taishan HU Zhujun YAO |
| |
| Institution: | 1. Department of Chemistry, Yunnan Nationalities University, Kunming, Yunnan 650031, China;2. State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China;3. Tel.: 0086‐021‐54925133;4. Fax: 0086‐021‐64166128 |
| |
| Abstract: | A stereoselective synthesis of all functionalized C2–C10 fragment 13 of the antitumor marine natural product clavulactone was accomplished, starting from the commercially available 3‐methylglutaric acid anhydride. Desymmetrization of 3‐methylglutaric acid anhydride with (S)‐α‐phenylethanamine was successfully employed as a key step to embed the isolated C8‐methyl group with the correct absolute configuration (99% de). The C3–C4 cis‐double bond was stereospecifically furnished by an RCM (ring‐closing metathesis) approach. Fragment 13 contains all preset functionalities and will be a useful precursor for the convergent total synthesis of clavulactone. |
| |
| Keywords: | clavulactone dolabellane desymmetrization ring‐closing metathesis stereoselectivity |
|
| 点击此处可从《中国化学》浏览原始摘要信息 |
| 点击此处可从《中国化学》下载免费的PDF全文 |
