- Fe-catalyzed synthesis of methyl-(2E,4Z)-deca-2,4-dienoate, a component of sex pheromones of Pityogenes chalcographus and Acanthoscelides obtectus
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Stereoselective synthesis of methyl-(2E,4Z)-deca-2,4-dienoate, a component of sex pheromones of Pityogenes chalcographus and Acanthoscelides obtectus, was performed on the basis of Fe-catalyzed cross-coupling of methyl-(2E,4Z)-5-chloropenta-2,4-dienoate with n-pentylmagnesium bromide.
- Shakhmaev,Sunagatullina, A. Sh.,Akimova,Zorin
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Read Online
- Palladium(ii)-catalyzed cross-coupling of simple alkenes with acrylates: A direct approach to 1,3-dienes through C-H activation
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The results from a direct palladium-catalyzed cross-coupling reaction between a variety of olefins with acrylate through vinylic C-H activation that give the corresponding butadienes in moderate to good yields and stereoselectivities are reported. Given the reaction's ability to tolerate a wide range of styrenes, aliphatic alkenes and acrylates, this atom- and step-economical methodology offers a straightforward method to forge new C-C bonds of the valuable diene products from readily available starting materials under very mild reaction conditions.
- Wen, Zhen-Kang,Xu, Yun-He,Loh, Teck-Peng
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p. 4520 - 4524
(2013/11/19)
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- Pheromone synthesis. Part 249: Syntheses of methyl (R,E)-2,4,5- tetradecatrienoate and methyl (2E,4Z)-2,4-decadienoate, the pheromone components of the male dried bean beetle, Acanthoscelides obtectus (Say)
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The enantiomers of methyl (E)-2,4,5-tetradecatrienoate (1), a component of the male pheromone of Acanthoscelides obtectus, were synthesized from the enantiomers of 1-undecyn-3-ol (6), which were obtained via asymmetric acetylation of (±)-1-trimethylsilyl-1-undecyn-3-ol (4) with vinyl acetate as catalyzed by lipase PS (Amano). The ortho ester Claisen rearrangement of 6 with triethyl orthoacetate was the key-step to generate the chiral allenic system. A new synthesis of (±)-1 was also executed starting from (±)-6. Three different syntheses of methyl (2E,4Z)-2,4-decadienoate (2), another component of the male pheromone of A. obtectus, were achieved by means of either palladium-catalyzed Heck reaction or a Claisen and an Al 2O3 catalyzed thermal rearrangements.
- Mori, Kenji
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experimental part
p. 1936 - 1946
(2012/04/10)
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- EXO- and endohormones. XXII1: Synthesis of methyl (2E,4Z)-2,4-decadienoate, the pheromone synergist of the bark beetle Pityogenes chalcographus
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The synthesis of methyl (2E,4Z)-2,4-decadienoate was based on a C 4 + C6 scheme. The coupling reaction took place between the 1-hexanale and phosphonium salt of methyl 1-bromocrotonate in a Wittig condensation. Methyl (2E,4Z)-2,4-decadienoate is a minor component of the sex pheromone of the bark beetle Pityogenes chalcographus.
- Maxim, Sanda,Ganscǎ, Lucia,Oprean, Ioan,Budae, Iuliana
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p. 543 - 544
(2007/10/03)
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- Bisexual attractants, aggregants and arrestants for adults and larvae of codling moth and other species of lepidoptera
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Novel bisexual attractants for lepidopterous insect pests isolated from pears or apples. A method for monitoring and control of codling moth and other species of Lepidoptera comprising a lure and kill, mating disruption or mass trapping strategy. A method of using a formulation containing the bisexual attractants with or without an insecticide and/or pheromone for control of the insect pests.
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- Stereoselective synthesis of methyl and ethyl (2E,4Z)-2,4-decadienoates from (E)-4,4-dimethoxy-2-butenal
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Methyl and ethyl (2E,4Z)-2,4-decadienoates were synthesized starting from (E)-4,4-dimethoxy-2-butenal.
- Ovanesyan,Garibyan,Badanyan
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p. 951 - 954
(2007/10/03)
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- Methyl (2E,4Z,6Z)-deca-2,4,6-trienoate, a thermally unstable, sex-specific compound from the stink bug Thyanta pallidovirens
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Sexually mature male stink bugs, Thyanta pallidovirens, release a male-specific blend of volatiles, including several sesquiterpene hydrocarbons, and the highly conjugated ester methyl (2E,4Z,6Z)-deca-2,4,6-trienoate 1. The latter compound was synthesized, and found to rearrange under GC conditions via a 1,7 sigmatropic rearrangement.
- Millar, Jocelyn G.
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p. 7971 - 7972
(2007/10/03)
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- SYNTHESIS AND CHARACTERIZATION OF ALL FOUR ISOMERS OF METHYL 2,4-DECADIENOATE FOR AN INVESTIGATION OF THE PHEROMONE COMPONENTS OF Pityogenes chalcographus
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Methyl (2E,4Z)-2,4-decadienoate (1), an important pheromone component of Pityogenes calcographus, and its three geometrical isomers (2-4) have been synthesized and obtained in >99percent isomeric purity.Urea inclusion complexes were used in the final purification procedures.Spectroscopic data (MS, (1)H and (13)C NMR) of all four isomers are discussed.A photoisomerization study of the decadienoates is presented.
- Baeckstroem, Peter,Jacobsson, Ulla,Norin, Torbjoern,Unelius, C. Rikard
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p. 2541 - 2548
(2007/10/02)
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- Stereoselective Synthesis of (2E,4E)- and (2Z,4E)-2,4-Alkadienoates by the Ester Enolate Claisen Rearrangement of (E)-1-Alkyl-3-trimethylsilyl-2-propenyl Glycolates Followed by the Peterson Reaction
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The ester enolate Claisen rearrangement of (E)-1-alkyl-3-trimethylsilyl-2-propenyl glycolates gave (E)-erythro-2-hydroxy-3-trimethylsilyl-4-alkenoates with high diastereoselectivity, which were stereoselectively converted into (2E,4E)- and (2Z,4E)-2,4-alkadienoates by the Peterson reaction.
- Sato, Toshio,Tsunekawa, Hiroshi,Kohama, Hiromasa,Fujisawa, Tamotsu
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p. 1553 - 1556
(2007/10/02)
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