1558-79-8Relevant academic research and scientific papers
Titanium(II)-based Z-reduction of alkynes. Syntheses of deuterium labelled linolenic and oleic acids and (3E,8Z,11Z)-tetradeca-3,8,11-trienyl acetate, the sex pheromone of a tomato pest, Scrobipalpuloides absoluta
Hungerford, Natasha L.,Kitching, William
, p. 1839 - 1858 (1998)
An operationally simple TiII-mediated, stereo- and regio-specific reduction of isolated, conjugated and methylene 'skipped' polyynes to the corresponding Z-polyenes in a one-pot procedure is described and applied inter alia to the syntheses of deuterium labelled linolenic and oleic acids. Final quenching with D2O (instead of H2O) results in regio- and stereo-specific Z-dideuteration of the alkyne. The synthesis of (3E,8Z,11Z)-tetradeca-3,8,11-trienyl acetate, the major sex pheromone of Scrobipalpuloides absoluta, a destructive pest of tomatoes, and the (3Z,8Z,11Z)-isomer, utilises this methodology in key reduction steps, and under- or over-reduction are negligible.
Enantioselective Synthesis of 7(S)-Hydroxydocosahexaenoic Acid, a Possible Endogenous Ligand for PPARα
Zhang, Minhao,Sayyad, Ashik A.,Dhesi, Anmol,Orellana, Arturo
, p. 13621 - 13629 (2020/12/15)
We report the first total synthesis of the polyunsaturated fatty acid 7-hydroxydocosahexaenoic acid (7-HDHA) in racemic form and the enantioselective synthesis of 7-(S)-HDHA. Both syntheses follow a convergent approach that unites the C1-C9 and C10-C22 fragments using Sonogashira coupling and Boland reduction as key steps. These syntheses enabled the unambiguous characterization of this natural product for the first time and helped establish 7(S)-HDHA as a possible endogenous ligand for peroxisome proliferator-activated receptor alpha.
A tea canker-worm pheromone (Z, Z, Z) - 3, 6, 9 - triene synthetic method of eighteen carbon (by machine translation)
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, (2018/09/28)
The invention relates to a natural [...] pheromone component novel synthesis method, in particular relates to a tea canker-worm pheromone (Z, Z, Z) - 3, 6, 9 - eighteen carbon triene synthetic method, it has [...], is non-toxic and harmless, which belongs to the field of drug synthesis. The invention uses inexpensive and easily obtained a halopropynyl alcohol as the reaction of the starting material, in order to iodo reagent catalytic coupling reaction as a key step, after six-step reaction, smooth synthetic tea canker-worm pheromone (Z, Z, Z) - 3, 6, 9 - eighteen carbon triene, the operation is simple, low cost, easily obtained and cheap materials, mild reaction conditions, high yield, the large scale preparation. (by machine translation)
Synthesis of Rare Polyunsaturated Fatty Acids: Stearidonic and ω-3 Arachidonic
Golovanov,Ivanov,Groza,Myagkova
, p. 1038 - 1041 (2016/02/18)
Total chemical syntheses of the rare natural ω-3 C18 and C20 fatty acids, which possess potential antiinflammatory activity, were elaborated for subsequent studies of their biological activity.
METHODS FOR THE SYNTHESIS OF 13C LABELED DHA AND USE AS A REFERENCE STANDARD
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Page/Page column 19-20, (2013/06/05)
A method for preparing 13C labeled docosahexaenoic acid (DHA) represented by Formula A: The method comprises the conversion of 2-pentyn-l-ol to 13C labeled DHA by reaction with propargyl alcohol, 13C labeled propargyl alco
Concise synthesis of (8Z,11Z,14Z)-8,11,14-heptadecatrienal, (7Z,10Z,13Z)-7,10,13-hexadecatrienal, and (8Z,11Z)-8,11-heptadecadienal, components of the essential oil of marine green alga Ulva pertusa
Akakabe, Yoshihiko,Washizu, Kensuke,Matsui, Kenji,Kajiwara, Tadahiko
, p. 1348 - 1352 (2008/02/01)
The long-chain aldehydes, (8Z,11Z,14Z)-8,11,14-heptadecatrienal, (7Z,10Z,13Z)-7,10,13-hexadecatrienal, and (8Z,11Z)-8,11-heptadecadienal, were concisely synthesized by using Grignard coupling, catalytic hydrogenation with the Lindlar catalyst, and oxidation with Dess-Martin periodinane as the key steps. Particularly, (8Z,11Z,14Z)-8,11,14-heptadecatrienal and (7Z,10Z, 13Z)-7,10,13-hexadecatrienal both possessed a seaweed-like odor.
Total synthesis of marine oxylipin bacillariolides I-III
Miyaoka, Hiroaki,Tamura, Masahide,Yamada, Yasuji
, p. 8083 - 8094 (2007/10/03)
Marine oxylipin bacillariolides I-III were synthesized from (R)-malic acid, using diastereoselective one-pot formation of the chiral cyclopentane derivative from the anion of allyl phenyl sulfone and chiral epoxymesylate as the key reaction. (C) 2000 Elsevier Science Ltd.
Synthesis of cyclopentane-containing marine eicosanoid bacillariolide II
Miyaoka, Hiroaki,Tamura, Masahide,Yamada, Yasuji
, p. 621 - 624 (2007/10/03)
Marine eicosanoid bacillariolide II was synthesized from (R)-malic acid, involving the diastereoselective one-pot formation of chiral cyclopentane derivative 12 from the anion of allyl phenyl sulfone and chiral epoxymesylate 11 as the key step.
ISOLATION AND TOTAL SYNTHESIS OF THE MAJOR CONSTITUENT OF THE ROOTS OF CENTAUREA INCANA: APLOTAXENE
Cossy, J.,Aclinou, P.
, p. 7615 - 7618 (2007/10/02)
The major constituent of the petroleum ether extract of the root of Centaurea incana was identified as (8Z,11Z,14Z)-1,8,11,14-heptadecatetraene (Aplotaxene 1).A convergent and highly stereoselective synthesis of this compound is reported.
SYNTHESES OF OPTICALLY ACTIVE PHEROMONES WITH AN EPOXY RING, (+)-DISPARLURE AND BOTH THE ENANTIOMERS OF (3Z,6Z)-cis-9,10-EPOXY-3,6-HENEICOSADIENE
Mori, Kenji,Ebata, Takashi
, p. 3471 - 3478 (2007/10/02)
(+)-Disparlure 1 and both the enantiomers of (3Z,6Z)-cis-9,10-epoxy-3,6-heneicosadiene 2 were synthesized in optically pure forms employing the Sharpless asymmetric epoxidation as the key-step.The natural pheromone 2 isolated from Estigmene acrea was shown to possess (9S,10R)-stereochemistry.
