- Pheromone synthesis. Part 257: Synthesis of methyl (2E,4Z,7Z)-2,4,7-decatrienoate and methyl (E)-2,4,5-tetradecatrienoate, the pheromone components of the male dried bean beetle, Acanthoscelides obtectus (Say)
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Tandem Dess-Martin oxidation/Wittig reaction of (2Z,5Z)-2,5-octadien-1-ol yielded methyl (2E,4Z,7Z)-2,4,7-decatrienoate, a newly discovered pheromone component of the male dried bean beetle, while that of (±)-2,3-dodecadien-1-ol gave (±)-methyl (E)-2,4,5-tetradecatrienoate, the racemate of the known and major pheromone component. Methyl (2E,4E,7Z)-2,4,7-decatrienoate was also synthesized, which is the methyl ester of an acid metabolite of a green alga. Reduction of 2,5-octadiyn-1-ol with Zn-Cu/EtOH cleanly gave (2Z,5Z)-2,5-octadien-1-ol.
- Mori, Kenji
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supporting information
p. 5589 - 5596
(2015/08/03)
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- A nine carbon homologating system for skip-conjugated polyenes
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Ozonolysis of Z,Z,Z-cylonona-1,4,7-triene leads to a 1,9-difunctionalised Z,Z-3,6-nonadiene which is readily converted into a range of polyunsaturated pheromones and fatty acids.
- Mustafa, Hussein H.,Baird, Mark S.,Al Dulayymi, Juma'A R.,Tverezovskiy, Viacheslav V.
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- Total synthesis and bioactivities of two proposed structures of maresin
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Maresin is a potent anti-inflammatory lipid mediator derived from docosahexaenoic acid (DHA). A highly convergent total synthesis of two proposed structures of C7-epimeric maresins from the four known fragments was achieved in 17 steps. The three key coupling reactions were the BF3-mediated alkyne attack on the epoxide, chiral titanium complex-promoted enantioselective alkyne addition to the aldehyde, and a Julia-Kocienski olefination. The two synthesized diastereomers were found to be comparably active in blocking neutrophil infiltration in the acute peritonitis model. Copyright
- Sasaki, Kenji,Urabe, Daisuke,Arai, Hiroyuki,Arita, Makoto,Inoue, Masayuki
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experimental part
p. 534 - 543
(2011/10/12)
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- Clean and Efficient Oxidation of Homoallylic and Homopropargylic Alcohols into β,γ-Unsaturated Aldehydes by The Dess-Martin Periodinane
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We describe the first efficient oxidation of homoallylic and homopropargylic alcohols to the corresponding very sensitive and unstable β,γ-unsaturated aldehydes by using Dess-Martin periodinane with a new neutral and anhydrous extraction protocol.
- Wavarin, Laurence,Viala, Jacques
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p. 326 - 330
(2007/10/03)
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- Antioxidant behaviour of thia fatty acids
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Eight thia fatty acids and other sulfides have been studied as inhibitors of autoxidation of arachidonic acid. The inhibitors extend the lag phase of the oxidation, to varying degrees. A carboxyl group in the vicinity of the sulfur reduces the antioxidant activity, while unsaturated sulfides are more effective than their saturated analogues. The results are consistent with the sulfides acting to reduce fatty acid hydroperoxides, which otherwise accumulate during the early stages of reaction and propagate the free-radical oxidation process.
- Easton, Christopher J.,Ferrante, Antonio,Robertson, Thomas A.,Xia, Ling
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p. 647 - 653
(2007/10/03)
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- Direct preparation of (Z,Z)-1,4-dienic units with a new C6 homologating agent: Synthesis of α-linolenic acid
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Syntheses of two C6 homologating agents 2a and 2f are described. These agents allow direct access to the (Z,Z)-1,4-diene unit 3, a moiety present in a wide number of natural compounds. Compound 2a is prepared in 40% overall yield by selective epoxidation of methoxycyclohexa-1,4-diene followed by oxidative ring cleavage and transatalization. Compound 2f is obtained in 90% yield by a one-step oxidative dimerization of phosphonium salt 1. A short synthetic application of these two new C6 homologating agents to the synthesis of α-linolenic acid is described.
- Sandri,Viala
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p. 271 - 275
(2007/10/02)
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- First total synthesis of a barnacle hatching factor 8(R)-Hydroxy-eicosa-5(Z),9(E),11(Z),14(Z),17(Z)-pentaenoic acid
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The first total synthesis of a barnacle hatching factor (BHF) establishes its constitution and absolute stereochemistry as 8(R)-Hydroxy-eicosa-5(Z),9(E),11(Z),14(Z),17(Z)-pentaenoic acid 1.
- Shing, Tony K.M.,Gibson,Wiley, Jonathan R.,Watt, C. Ian F.
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p. 1067 - 1070
(2007/10/02)
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- Total Stereospecific Synthesis of all cis-5,8,11,14,17-Eicosapentaenoic Acid (EPA)
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Total stereospecific synthesis of EPA has been performed by a sequence of ozonolysis, selective reduction and Wittig reactions which affords the cis-skipped olefinic system.Versatile compound 4, readily prepared from dihydro anisole, allowed us to prepare the skipped dienic synthon 2 in high yield.Key Words: All cis-eicosapentanoic acid, EPA, cis-Wittig reaction, Ozonolysis.
- Viala, Jacques,Sandri, Jacqueline
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p. 4897 - 4900
(2007/10/02)
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