Stereoselective Synthesis of(5Z,7E)-Dodecadien-1-ol

Abstract

Abstract: Sexpheromone of Dendrolimus Spp. is composed of (5Z, 7E)-5,7-Dodecadien-1-ol(1) and its acetate and propionate. At first 7-bromo-(4Z, 6E)-heptadien-1-al(2) was stereoselectively synthesized by the tandem addition reaction of acrolein with acetylene in the presence of Pd(OAc)₂. Novel stereoselective synthesis of (5Z, 7E)-5,7-Dodecadien-1-ol was achieved in five steps, using palladium-catalyzed coupling reaction of 7-bromo-(4Z, 6E)-4,6-heptadiene-1-al ethylene acetal from production of the above aldehyde with Grignard reagent as the key step. The structures of all the compounds were confirmed by IR, NMR and MS spectra.

Key words: Dendrolimus Spp, (5Z,7E)-Dodecadien-1-ol, Stereoselective synthesis, Coupling-reaction, Palladium catalyst

CLC Number:

O623

TrendMD:

TAO Yun-Hai, CHENG Wei-Xian, ZHANG Yu-Shun, GU Kun, . Stereoselective Synthesis of(5Z,7E)-Dodecadien-1-ol[J]. Chem. J. Chinese Universities, 2005, 26(6): 1072.

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Stereoselective Synthesis of(5Z,7E)-Dodecadien-1-ol

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