Herbarumin Ⅲ的立体选择性全合成

Convenient Stereoselective Approach to Herbarumin Ⅲ

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.