Simple total synthesis of juvenile honnone analogue - Isopropyl 11-methoxy-3,7,11-tirimethyl-2,4-dodecadienoate

文献类型： 外文期刊

第一作者： Zhu, XH

作者： Zhu, XH;Jiang, HF;Tian, XS;Ran, XG

作者机构：

关键词： juvenile hormone analogue;isopropyl 11-methoxy-3,7,11-trimethyl-2,4-dodecadienoate;citronellal;Wittig-Homer reaction;total synthesis

期刊名称：CHINESE JOURNAL OF ORGANIC CHEMISTRY （ 影响因子：1.652； 五年影响因子：1.2 ）

ISSN： 0253-2786

年卷期： 2004 年 24 卷 6 期

页码：

收录情况： SCI

摘要： Isopropyl-4-bromo-3-methyl-2-butenoate was prepared from initial acetone via condensation, dehydrolysis, oxidation, esterification and bromination. Then, reaction of the synthesized isopropyl-4-bromo-3-methyl-2-butenoate with triethyl phosphite provided Wittig-Homer reagent. Subsequently, Wittig-Homer reaction of the Wittig-Homer reagent with citronellal was carried out, and followed by the etherification with methanol catalyzed by cation exchange resin, to finally give isopropyl-11-methoxy-3,7,11-trimethyl-2,4-dodecadienoate with Juvenile hormone activity. The 2E,4E stereoisomer (over 66% yield) showed considerably higher activity than other isomers. The structures of all the compounds were confirmed by H-1 NMR, IR and MS spectra.

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