| Herbarumin Ⅲ的立体选择性全合成 |
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| 引用本文： | 陈雪松,达世俊,许柏岩,谢志翔,李瀛.Herbarumin Ⅲ的立体选择性全合成[J].高等学校化学学报,2007,28(11):2086-2091. |
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| 作者姓名： | 陈雪松 达世俊 许柏岩 谢志翔 李瀛 |
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| 作者单位： | 兰州大学化学化工学院,功能有机分子化学国家重点实验室,兰州,730000 |
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| 摘 要： | 以正丁醛和1,5-戊二醇为起始原料, 以不对称烯丙基化、改良的Julia成烯反应和Yamaguchi内酯化为关键步骤, 通过13步反应, 立体选择性地合成了具有植物毒性的天然十元内酯化合物Herbarumin Ⅲ(3)及其差向异构体22.
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| 关 键 词： | Herbarumin Ⅲ 不对称烯丙基化 改良的Julia成烯反应 Yamaguchi内酯化 |
| 文章编号： | 0251-0790（2007）11-2086-06 |
| 收稿时间： | 2007-01-23 |
| 修稿时间： | 2007-01-23 |
Convenient Stereoselective Approach to Herbarumin Ⅲ |
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| CHEN Xue-Song,DA Shi-Jun,XU Bo-Yan,XIE Zhi-Xiang,LI Ying.Convenient Stereoselective Approach to Herbarumin Ⅲ[J].Chemical Research In Chinese Universities,2007,28(11):2086-2091. |
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| Authors: | CHEN Xue-Song DA Shi-Jun XU Bo-Yan XIE Zhi-Xiang LI Ying |
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| Institution: | The State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering Lanzhou Univesirtry, Lanzhou 730000, China |
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| Abstract: | Herbarumin Ⅲ, a naturally occurred phytotoxin which has a ten-membered lactone ring, was isolated from Phoma herbarum. The root growth inhibiting activity of Herbarumin Ⅲ is ten times than 2,4-dichlorophenoxyacetic acid. The stereoselective total synthesis of Herbarumin Ⅲ (3), along with its 8-epimer 22, was succeeded in 13 steps starting from n-butyraldehyde and 1,5-pentandiol on the bassis of Brown's asymmetric allylation, with modified Julia olefination and Yamaguchi's macro-lactonization as the key steps. |
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| Keywords: | Herbarumin Ⅲ Asymmetric allylation Modified Julia olefination Yamaguchi’s macro-lactonization |
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