Herbarumin Ⅲ的立体选择性全合成  

Convenient Stereoselective Approach to Herbarumin Ⅲ

作　　者：陈雪松[1] 达世俊[1] 许柏岩[1] 谢志翔[1] 李瀛[1] 

机构地区：[1]兰州大学化学化工学院

出　　处：《高等学校化学学报》2007年第11期2086-2091,共6页Chemical Journal of Chinese Universities

基　　金：国家自然科学基金(批准号:20672050)资助

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.Herbarumin Ⅲ, a naturally occurred phytotoxin which has a ten-membered lactone ring, was isolated from Phoma herbarurn. The root growth inhibiting activity of Herbarumin Ⅲ is ten times than 2,4-dichloro- phenoxyacetic 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.

关 键 词：Herbarumin Ⅲ 不对称烯丙基化 改良的Julia成烯反应 Yamaguchi内酯化 

分 类 号：O621.34[理学—有机化学]