THE SYNTHESIS OF THE 1ST NATURAL HOST GERMINATION STIMULANT FOR STRIGA-ASIATICA (WITCHWEED)

被引:19
作者
SARGENT, MV
WANGCHAREONTRAKUL, S
机构
[1] Department of Organic Chemistry, University of Western Australia, Nedlands
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1990年 / 05期
关键词
D O I
10.1039/p19900001429
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of 5-methoxy-3-(8′Z,11′Z)-pentadeca-8′, 11′,14′-trienylbenzene-1,2,4-triol (18), a germination stimulant for Striga asiatica (witchweed), isolated from Sorghum bicolor, is reported. The key step was a (Z)-stereoselective Wittig reaction between the ylide derived from 3-(Z)-hepta-3,6-dien-1-yltriphenylphosphonium iodide (7) and 8-(2,3,6-triacetoxy-5-methoxyphenyl)octanal (16). The synthesis of the structurally related catechol, 3-(8′Z,11′Z)-pentadeca-8′, 11′,14′-trienylbenzene-1,2-diol (22), which occurs in the Anacardaceous species, Toxicodendron radicans (poison ivy), is also reported.
引用
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页码:1429 / 1434
页数:6
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