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-Horner reagent. Subsequently, Wittig-Horner reaction of the Wittig-Horner reagent with citronellal was carried out, and followed by the etherification with methanol catalyzedby 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 ¹H NMR, IR and MSspectra.

Key words: juvenile hormone analogue, isopropyl 11-methoxy-3,7,11-trimethyl-2,4-dodecadienoate, citronellal, Wittig-Horner reaction, total synthesis