Synthesis of melampolides and cis,cis-germacranolides as natural herbicide models

被引：18

作者：

Macías, FA

Velasco, RF

Alvarez, JA

Castellano, D

Galindo, JCG

机构：

[1] Univ Cadiz, Grp Alelopatia, Dept Quim Organ, Fac Ciencias, Cadiz 11510, Spain

[2] Univ Cadiz, Dept Quim Fis, Fac Ciencias, Cadiz 11510, Spain

来源：

TETRAHEDRON | 2004年 / 60卷 / 38期

关键词：

allylic oxidation mechanism; synthesis of sesquiterpenes; melampolides; cis; cis-germacranolides; structure-activity relationship study (SAR);

D O I：

10.1016/j.tet.2004.06.128

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The comparative study between the theoretical molecular properties of the starting materials and the yields in the transformation of melampolides to cis,cis-germacranolides using SeO2/t-BuOOH (TBHP) as oxidant allows to establish a feasible relationship with their values of dipolar moment. Conditions for this transformation are optimized and some mechanistic considerations are made based in this finding. Cluster analysis of the phytotoxic activity of the melampolides and cis, cis-germacranolides obtained shows that the activity is greatly influenced by the spatial shape of the backbone, prevailing upon other factors such as the presence of reactive functional groups. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：8477 / 8488

页数：12

共 38 条

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