- Method for preparation of Octadecadienyl acetate as major sex pheromone of cherry tree borer, Synanthedon bicingulate
-
The present invention relates to a method for producing a sex pheromone of cherry tree borer (Synanthedon bicingulata) in an attempt to control the same. More specifically, provided is a method for stereoselectively producing high purity (3E,13Z)- octadecadienyl acetate and (3Z,13Z)-octadecadienyl acetate respectively which are major sex pheromones of cherry tree borer from a cheap starting material in an efficient, simple, and economically feasible way.COPYRIGHT KIPO 2018
- -
-
Paragraph 0078-0082
(2018/06/26)
-
- Synthesis and characterization of 3,13- and 2,13-octadecadienyl compounds for identification of the sex pheromone secreted by a clearwing moth, Nokona pernix
-
Several geometrical isomers of 3,13- and 2,13-octadecadien-1-ols and their acetates were synthesized starting from 1,8-octanediol or 1,9-nonanediol utilizing acetylene coupling reactions. In addition to commercially available compounds, all geometrical isomers of each dienyl compound were analyzed by NMR and GC-MS to accumulate chemical data for studies of sex pheromones secreted from clearwing moths classified into the family Sesiidae of Lepidoptera. Although acetoxy derivatives of the 3,13- and 2,13-dienes showed almost the same mass spectra, the alcohols were distinguished by comparing the relative intensities of [M - 18]+ at m/z 248, indicating direct differentiation of the two positional isomers without derivatization. Furthermore, each geometrical isomer eluted from a high-polar GC column with a different retention time. Base on these data, a pheromone gland extract of a sesiid moth, Nokona pernix, was analyzed by GC-EAD and GC-MS, and two EAG-active components were identified, viz., the (3E,13Z)- and (3Z,13Z)-isomers of 3,13-octadecadien-1-ol in a ratio of 9:1. In the field, the synthetic compounds mixed in 9:1 ratio attracted N. pernix males well, while a single component scarcely attracted the males. The number of attracted males peaked in the middle of June, and a small second peak was observed in August.
- Naka, Hideshi,Nakazawa, Tomotake,Sugie, Mieko,Yamamoto, Masanobu,Horie, Yoshiteru,Wakasugi, Ryohei,Arita, Yutaka,Sugie, Hajime,Tsuchida, Koji,Ando, Tetsu
-
p. 508 - 516
(2008/02/10)
-
- A convergent and highly efficient synthesis of (E,Z)-2,13-octadecadienyl acetate and (E,Z)-3,13-octadecadienyl acetate, components of the sex pheromone of the Leopard Moth Zeuzera pyrina, through sulfones
-
(equation presented) A new, convergent synthesis of (E,Z)-2,13-octadecadienyl acetate (1) and (E,Z)-3,13-octadecadienyl acetate (2), the two key components of the leopard moth Zeuzera pyrina, from 2-chloromethyltetrahydrofuran in good overall yields and stereomeric purity is reported. The synthesis of both components utilizes the common intermediate sulfone 12 as a convenient building block to be coupled with iodoacetylenic derivatives 9 or 17 in the key step.
- Capdevila, Anna,Prasad, Attaluri R.,Quero, Carmen,Petschen, Ine?s,Bosch, Maria P.,Guerrero, Angel
-
p. 845 - 848
(2008/02/09)
-
- SYNTHESIS OF TRANS-2,CIS-13- AND TRANS-3,CIS-13-OCTADECADIEN-1-OL ACETATES, COMPONENTS OF THE SEX PHEROMONE OF SYNANTHEDON TIPULIFORMIS (LEPIDOPTERA, SISIIDAE)
-
The Wittig-Horner reaction of ethoxycarbonylmethylenetriphenylphosphorane or ethyl diethylphosphonoacetic acid with cis-11-hexadecenal and the modified Knoevenagel reaction of this aldehyde with malonic acid gave the ethyl ester of trans-2,cis-13-octadecadienoic acid and trans,cis-13-octadecadienoic acid, which upon reduction and acetylation were converted into trans-2,cis-13- and trans-3-cis-13-octadecadien-1-yl acetates, which are components of the sex pheromone of Synanthedon tipuliformis (Lepidoptera, Sisiidae).
- Sorochinskaya, A.M.,Kovalev, B.G.
-
p. 621 - 624
(2007/10/02)
-
- Stereoselective synthesis of (Z,Z)-3, 13-octadecadien-1-ol, (Z,Z)-3, 13-octadecadien-1-yl acetate and their (E,Z)isomers
-
(Z,Z)-3,13-Octadecadien-1-ol (VIII), (Z,Z)-3,13-octadecadien-1-yl acetate (IX) and their corresponding (E,Z) isomers (X and XI) have been synthesized via Li2CuCl4 catalysed coupling reaction of (Z)-8-tridecylmagnesium bromide with mesylate (II) as a key step.
- Trehan, I R,Kad, G L,Singh, Vasundhara,Vig, Rakesh
-
p. 563 - 566
(2007/10/02)
-
- EFFICIENT SYNTHESIS OF 3E,13Z-OCTADECADIENOL, ITS ACETATE, 4E,6E,11Z-HECADECATRIENAL, AND 4E,6E,11Z-HEXADECATRIENYL ACETATE, SEX PHEROMONES OF SOME LEPIDOPTERAN SPECIES
-
The title linear acetogenins have been synthesized by a strategy of joining acetylcyclopropane to 8Z-tridecenol or 5Z-decenol prepared after Julia, leading to the corresponding secondary cyclopropylcarbinols.The ZnBr2/Me3SiBr-initiated homoallylic rearrangement of the latter assures at a key step the stereospecific construction of transoid fragments of the target molecules.
- Ivanova, N. M.,Cheskis, B. A.,Moiseenkov, A. M.,Nefedov, O. M.
-
p. 2196 - 2204
(2007/10/02)
-
- Acetylcyclopropane as a Five-Carbon Building Block in the Synthesis of some Acetogenin Insect Pheromones
-
Interaction of deprotonated acetylcyclopropane cyclohexylimine with several aliphatic alkyl halides, epoxides, and aldehydes efficiently gave the corresponding cyclopropyl ketones.Some of the respectible alcohols were rearranged in a highly stereoselective manner under the action of trimethylsilyl bromide in the presence of zinc bromide into the corresponding linear (E)-homoallyl bromides.The latter were used, in turn, as key intermediates in concise syntheses of thirteen terminally functionalized straight-chain oligoolefins which are known to constitute acetogenin pheromonal components for more than 65 species of lepidopteran insects.
- Moiseenkov, Alexander M.,Czeskis, Boris A.,Ivanova, Natalya M.,Nefedov, Oleg M.
-
p. 2639 - 2649
(2007/10/02)
-
- A CONVENIENT SYNTHESIS OF 2,13- AND 3,13-OCTADECADIENYL ACETATES, SEX PHEROMONE COMPONENTS OF THE Synanthedon SPECIES
-
The sex pheromone components of several Synanthedon species, 2,13- and 3,13- octadecadienyl acetates (Ic, Id, IIc, IId), have been synthesized following the acetylenic route of chain elongation.Starting from ω-alkyn-1-ols III, the final compounds were constructed in five steps in about 30percent overall yields.Transformation of triple bond containing intermediates into the corresponding (Z)- and (E)-olefins was achieved either by hydrogenation over the P2-Ni catalyst or by using a dispersion of sodium in toluene.The title pheromones were generated in more than 97percent stereoisomeric purity. 1H and 13C NMR data of all derivatives are included.
- Hoskovec, Michal,Saman, David,Koutek, Bohumir
-
p. 2270 - 2281
(2007/10/02)
-
- SIMPLE AND STEREOCONTROLLED SYNTHESIS OF AN OPTIMAL ISOMERIC MIXTURE OF 3,13-OCTADECADIEN-1-YL ACETATES
-
A simple route has been developed for the preparation of the optimal isomeric mixture of 3,13-octadecadien-1-yl acetates (ODDA) which is the active sex pheromone of many Synanthedon species.The stereocontrolled formation of double bonds have been achieved via Wittig reaction and subsequent reduction of C-C triple bond.
- Vinczer, Peter,Baan, Gabor,Juvancz, Zoltan,Novak, Lajos,Szantay, Csaba
-
p. 1257 - 1270
(2007/10/02)
-
