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
作者： Zhu, XH 1 ; Jiang, HF 2 ; Tian, XS 2 ; Ran, XG 2 ;
作者机构： 1.Chinese Acad Sci, Guangzhou Inst Chem, Guangzhou 510650, Peoples R China
2.Chinese Acad Sci, Guangzhou Inst Chem, Guangzhou 510650, Peoples R China; Guangdong Acad Agr Sci, Agr Biotechnol Res Inst, Guangzhou 510640, Peoples R China
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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