Agricultural and Biological Chemistry
Online ISSN : 1881-1280
Print ISSN : 0002-1369
ISSN-L : 0002-1369
Stereoselective Synthesis of Some Isomers of Dodecadien-1-ol: Compounds Related to the Pine Moth Sex Pheromone
Tetsu ANDManh HUYNH VUShigeo YOSHIDANobutaka TAKAHASHI
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1982 年 46 巻 3 号 p. 717-722

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Four isomers of 5, 7-dodecadien-1-ol were previously proposed as being the sex pheromone of the pine moth. The isomers were stereoselectively synthesized from 1-hexyne and tetrahydropyranyl ether of 5-hexyn-1-ol. The (5Z, 7Z)-isomer was synthesized by a Chodkiewic Cadiot reaction followed by hydroboration, and other three isomers by novel synthetic methods including the addition of zirconocene hydride [Schwarz's reagent (C5H5)2Zn(H)Cl] to control the regioselective coupling reaction. The 5, 8- and 5, 9-dodecadien-1-ols were also synthesized by similar methods for comparison of their characteristics with the endogenous sex pheromone.
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© Japan Society for Bioscience, Biotechnology, and Agrochemistry
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