• Journal of the Korean Chemical Society
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• v.31 no.6
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• pp.576-581
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• 1987

Synthesis and Biological activity test are described for the (E)-11-tetradecen-1-yl acetate and (Z)-11-tetradecen-1-yl acetate, the sex pheromone of the Asiatic leafroller moth (Archippus breviplicanus Walsingham). 10-Bromodecan-1-ol THP ether was prepared from 10-bromodecan-1-ol. In liquid ammonia with THF and HMPA as cosolvents, sodium acetylide could be alkylated with 10-bromodecan-1-al THP ether to give 11-dodecyn-1-ol THP ether. 11-Dodecyn-1-ol THP ether was then treated with n-Buli in THF to give the lithium acetylide, which was alkylated with bromoethane to afford 11-tetradecyn-1-ol THP ether. 11-Tetradecyn-1-ol THP ether was then reduced over $Pd/BaSO_4$ and with Na in liquid $NH_3$ to give (Z)-11-tetradecen-1-ol THP ether and (E)-11-tetradecen-1-ol THP ether, respectively. (Z)-and (E)-11-Tetradecen-1-ol THP ether thus obtained were deprotected by refluxing in the presence of PPTS and ethanol. (Z)-and (E)-11-tetradecen-1-ol were acetylated with acetic anhydride to afford the final products, (Z)-11-tetradecen-1-yl acetate (1) and (E)-11-tetradecen-1-yl acetate (2), respectively. The synthetic pheromone thus obtained was attractive to the males of the Asiatic leafroller moth in the field.

• Journal of the Korean Chemical Society
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• v.32 no.1
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• pp.65-70
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• 1988

Synthesis and biological activity test are described for the (Z)-9-tetradecen-1-yl acetate(1) and (Z)-11-tetradecen-1-yl acetate(1) and (Z)-11-tetradecen-1-yl acetate(2), the sex pheromone of the summer fruit tortrix moth, Adoxophyes orana. 8-Bromoctan-l-ol THP ether was prepared from 8-bromoctan-l-ol. The lithium anion of 1-hexyne was alkylated with 8-bromoctan-l-ol THP ether gave 9-tetradecyn-l-ol THP ether. Catalytic hydrogenation over Pd/BaSO4 followed by deprotection afforded (Z)-9-tetradecen-l-ol. Acetylation gave (Z)-9-tetradecen-1-yl acetate(1). l0-Bromodecan-l-ol THP ether was obtained from l0-bromodecan-l-ol. In liquid ammonia with THF and HMPA as cosolvents, sodium acetylide could be alkylated with 10-bromodecan-l-ol THP ether to give 11-dodecyn-l-ol THP ether. 11-Dodecyn-l-ol THP ether was then treated with n-BuLi in THF to give the lithium acetylide, which was alkylated with bromoethane to afford 11-tetradecyn-l-ol THP ether. Catalytic hydrogenation, deprotection, and acetylative gave (Z)-11-tetradecen-1-yl acetate(2). The synthetic pheromone thus obtained was attractive to the males of the summer fruit tortrix in the field.

• Journal of the Korean Chemical Society
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• v.32 no.1
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• pp.60-64
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• 1988

Synthesis and biological activity test are described for the (Z)-11-hexadecen-1-ol, (Z)-11-hexadecen-1-yl acetate, and (Z)-11-hexadecen-l-al, the sex pheromone of the diamond back moth, Plutella xylostella L.. Lithium acetylide was alkylated with 10-bromodecan-1-ol THP ether to give 11-hexadecyn-l-ol THP ether. 11-Hexadecyn-l-ol THP ether was stereoselectively reduced over Pd/BaSO4to yield (Z)-11-hexadecen-l-ol THP ether, which was in turn deprotected to provide (Z)-11-hexadecen-l-ol. (Z)-11-Hexadecen-l-ol was acetylated and oxidized to afford (Z)-11-hexadecen-1-yl acetate and (Z)-11-hexadecen-l-al, respectively. Biological activity test of the synthetic compounds, (Z)-11-hexadecen-l-ol, (Z)-11-hexadecen-1-yl acetate, and (Z)-11-hexadecen-l-al in the ratio of 0.1 : 5 : 5 was tested in the field using polyethylene capsules as containers. The numbers of moth trapped with pheromone vials were counted.

• Bulletin of the Korean Chemical Society
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• v.28 no.1
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• pp.103-107
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• 2007

A mild, chemoselective and convenient method for the formation and deprotection of tetrahydropyranyl ethers is described. With 1-5 mol% of acetyl chloride and slightly excess dihydropyran in methylene chloride or in neat dihydropyran, the formation of THP ethers from the corresponding alcohols was accomplished in the presence of many acid-sensitive functional groups. Efficient cleavage of THP ethers was also accomplished with the same reagent by switching the solvent to methanol.

• Bulletin of the Korean Chemical Society
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• v.8 no.4
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• pp.235-237
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• 1987

(7Z, 11E)-7, 11-Hexadecadien-1-yl acetate(1), the sex pheromone of the female Angoumois grain moth, Sitotroga cerealella, was synthesized via the acetylenic intermediate, (11E)-11-hexadecen-7-yn-ol THP ether(2). The acetylenic compound was prepared from 7-octyn-1-ol THP ether(4) and (3E)-1-bromo-3-octene(3). The (E)-homoallylic bromide 3 was synthesized by the Julia olefin synthesis of 1-cyclopropylpentan-1-ol(6).

• Bulletin of the Korean Chemical Society
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• v.6 no.1
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• pp.15-19
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• 1985

(Z)-12-Tetradecen-1-yl acetate (1), (E)-12-tetradecen-1-yl acetate (2) and tetradecan-1-yl acetate (3), the active components of the sex pheromone of the Asian Corn Borer moth were synthesized by two different methods, one from acetylene and 11-bromo-1-undecanol THP ether by acetylenic route, the other from 12-acetoxy-1-dodecanal and ethylidenetriphenylphosphonium ylide by Wittig route.