13280-07-4Relevant academic research and scientific papers
Synthesis and functional pharmacological effects on human bronchi of 20-hydroxyeicosatetraenoic acid
Proteau-Gagne,St-Jean,Morin,Gendron,Rousseau,Dory
, p. 841 - 847 (2011)
We have synthesized 20-hydroxyeicosatetraenoic acid (20-HETE) following a new route and delineated its functional effects in human bronchi. Isometric tension measurements were performed, and they demonstrated that synthetic 20-HETE induced a concentration-dependent relaxant effect in ASM on resting tone and on bronchi pre-contracted with methacholine.
Synthesis and Characterization of Cyanobutadiene Isomers-Molecules of Astrochemical Significance
Esselman, Brian J.,Hyland, Grace E.,Knezz, Stephanie N.,Kougias, Samuel M.,Lee, Daniel J.,McMahon, Robert J.,Owen, Andrew N.,Patel, Aatmik R.,Sanchez, Rodrigo A.,Woods, R. Claude
, (2020)
Four cyanobutadiene isomers of considerable interest to the organic chemistry, molecular spectroscopy, and astrochemistry communities were synthesized in good yields and isolated as pure compounds: (E)-1-cyano-1,3-butadiene (E-1), (Z)-1-cyano-1,3-butadiene (Z-1), 4-cyano-1,2-butadiene (2), and 2-cyano-1,3-butadiene (3). A diastereoselective synthesis was developed to generate (E)-1-cyano-1,3-butadiene (1) (10:1 E/Z) via tandem SN2 and E2′ reactions. The potential energy surfaces of the E2′ reactions leading to (E)- A nd (Z)-1-cyano-1,3-butadiene (1) were analyzed by density functional theory calculations, and the observed diastereoselectivity was rationalized in the context of the Curtin-Hammett principle. The preparation of pure samples of these reactive compounds enables measurement of their laboratory rotational spectra, which are the critical data needed to search for these species in space by radioastronomy.
Rhodium-Catalyzed Enantioselective Cyclization of 3-Allenyl-indoles: Access to Functionalized Tetrahydrocarbazoles
Grugel, Christian P.,Breit, Bernhard
, p. 5798 - 5802 (2019)
A highly selective rhodium-catalyzed cyclization of tethered 3-allenylindoles is reported. In a smooth reaction, 1-vinyltetrahydrocarbazoles are obtained in excellent yields and enantioselectivities. Aside from a great functional group tolerance, this method requires neither the Schlenk technique nor the use of anhydrous solvents. Preliminary mechanistic investigations proved that the reaction proceeds via an intermediary formed spiroindolenine which rapidly undergoes an acid-catalyzed stereospecific migration.
Dearomative Cycloadditions Utilizing an Organic Photosensitizer: An Alternative to Iridium Catalysis
Rolka, Alessa B.,Koenig, Burkhard
, p. 5035 - 5040 (2020)
A highly efficient, cheap, and organic alternative to the commonly used iridium photosensitizer (Ir[dF(CF3)ppy]2(dtbpy))PF6 ([Ir-F]) is presented for visible-light energy transfer catalysis. The organic dye 2CzPN surpasses [Ir-F] in selectivity while at t
REACTIVE, LIPOPHILIC NUCLEOSIDE BUILDING BLOCKS FOR THE SYNTHESIS OF HYDROPHOBIC NUCLEIC ACIDS
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Paragraph 0441, (2019/06/20)
The present invention relates to a method for the isolation and/or identification of known or unknown sequences of nucleic acids (target sequences) optionally marked with reporter groups by base specific hybridation with complementary sequences using nucleolipids. The nucleolipids are prepared by lipophilizing nucleosides of formula (Ia) wherein Q represents a group having a substituted tetrahydrofuran ring and Bas represents a group having one or more heterocyclic rings having one or more heterocyclic nitrogen atoms.
Rhodium-Catalyzed Diastereo- And Enantioselective Tandem Spirocyclization/Reduction of 3-Allenylindoles: Access to Functionalized Vinylic Spiroindolines
Grugel, Christian P.,Breit, Bernhard
supporting information, p. 9672 - 9676 (2019/12/24)
A highly selective rhodium-catalyzed tandem spirocyclization/reduction of 3-allenylindoles is reported. By employing a Hantzsch ester as reductant, vinylic spiroindolines are obtained in excellent yields as well as diastereo- and enantioselectivity. In addition, the reaction's synthetic utility is highlighted by broad functional group compatibility and exemplified by a gram scale reaction with subsequent assorted transformations.
Selective Cascade Reaction of Bisallenes via Palladium-Catalyzed Aerobic Oxidative Carbocyclization–Borylation and Aldehyde Trapping
Naidu, Veluru Ramesh,Posevins, Daniels,Volla, Chandra M. R.,B?ckvall, Jan-E.
supporting information, p. 1590 - 1594 (2017/02/05)
A cascade reaction, consisting of a palladium-catalyzed regioselective aerobic oxidative carbocyclization–borylation of bisallenes and a final aldehyde trapping, afforded triene alcohols with high diastereoselectivity. The cascade reaction occurs under mild reaction conditions and proceeds via an allylboron intermediate that is trapped by the aldehyde in a stereoselective manner.
Stereoselective synthesis of 17,18-epoxy derivative of EPA and stereoisomers of isoleukotoxin diol by ring opening of TMS-substituted epoxide with dimsyl sodium
Nanba, Yutaro,Shinohara, Riku,Morita, Masao,Kobayashi, Yuichi
supporting information, p. 8614 - 8626 (2017/10/27)
The reaction of TMS-substituted epoxy alcohols (and derivatives) with dimsyl sodium (NaDMSO) to give 1-alkene-3,4-diols was used for the synthesis of enantiomerically enriched 17(R),18(S)-EpETE and two diastereoisomers of isoleukotoxin diol. In the synthesis of 17(R),18(S)-EpETE, the α-ethoxyethyl ether (EE) of the epoxy alcohol derived from (R)-1-TMS-1-penten-3-ol underwent reaction with NaDMSO to give the mono EE-protected 1-hexene-3,4-diol. The aldehyde obtained by hydroboration/oxidation was subjected to Wittig reaction to afford a mono EE-protected diol. The corresponding mono mesylate was prepared and subjected to epoxide ring formation to afford 17(R),18(S)-EpETE stereoselectively. Similarly, a reaction of the anti epoxy alcohol derived from (R)-1-TMS-1-octen-3-ol with NaDMSO gave the anti form of 1-nonene-3,4-diol, which was converted to 12(S),13(R)-isoleukotoxin diol through Wittig reaction. 12(R),13(R)-Isoleukotoxin diol was synthesized in a similar manner.
Synthesis and discovery of phytofurans: metabolites of α-linolenic acid peroxidation
Cuyamendous,Leung,Durand,Lee,Oger,Galano
supporting information, p. 15696 - 15699 (2015/11/02)
Phytofurans are novel metabolites produced by non-enzymatic peroxidation of α-linolenic acid. An unprecedented Payne rearrangement-cyclization of a C2-symmetric bis-epoxide permitted construction of the core 3-hydroxy-2,5-disubstituted tetrahydrofuran. LC-MS/MS investigation provided evidence for the presence of phytofurans in nuts and seeds for the first time.
Highly functionalized donor-acceptor cyclopropanes applied toward the synthesis of the Melodinus alkaloids
Goldberg, Alexander F.G.,Craig, Robert A.,O'Connor, Nicholas R.,Stoltz, Brian M.
supporting information, p. 2983 - 2990 (2015/05/27)
Abstract A series of highly substituted vinylcyclopropanes were prepared and examined as reaction partners in a palladium-catalyzed (3+2) cycloaddition with nitrostyrenes. Described herein are our efforts to synthesize an elusive 1,1-divinylcyclopropane by several distinct approaches, and to apply surrogates of this fragment toward the synthesis of the Melodinus alkaloids.
