高等学校化学学报

高等学校化学学报

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Herbarumin Ⅲ的立体选择性全合成

陈雪松, 达世俊, 许柏岩, 谢志翔, 李瀛   

  1. CHEN Xue-Song, DA Shi-Jun, XU Bo-Yan, XIE Zhi-Xiang, LI Ying*
  • 收稿日期:2007-01-23 修回日期:1900-01-01 出版日期:2007-11-10 发布日期:2007-11-10
  • 通讯作者: 李瀛

Convenient Stereoselective Approach to Herbarumin Ⅲ

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   

  1. The State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou Univesirtry, Lanzhou 730000, China
  • Received:2007-01-23 Revised:1900-01-01 Online:2007-11-10 Published:2007-11-10
  • Contact: LI Ying

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被引次数

2

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.

关键词: Herbarumin Ⅲ, 不对称烯丙基化, 改良的Julia成烯反应, Yamaguchi内酯化

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.

Key words: Herbarumin Ⅲ, Asymmetric allylation, Modified Julia olefination, Yamaguchi’s macro-lactonization

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