122952-20-9Relevant articles and documents
Mass Spectra of Substituted Butenolides
Lin, Shaw-Tao,Kuo, Yueh-Hsiung,Wang, Eng-Chi,Lin, Wen-Chung
, p. 129 - 132 (1997)
The mass spectra of a series of substituted butenolides were studied. Their fragmentations in the mass spectrometer strongly depend upon the nature of the substitutents. The fragment's ions include the lactone skeletons, substituents, and resultant derive
Lipase catalyzed dynamic kinetic resolution of some 5-hydroxy-2(5H)-furanones
Thuring, Jan Willem J. F.,Klunder, Antonius J. H.,Nefkens, Gerard H. L.,Wegman, Margreth A.,Zwanenburg, Binne
, p. 4759 - 4760 (1996)
Lipase PS was successfully applied in the dynamic kinetic resolution of 5-hydroxy-2(5H)-furanones 4a-d (quantitative conversions, e.e.'s 78-86%).
Total Synthesis of (-)-Chromodorolide B
Tao, Daniel J.,Slutskyy, Yuriy,Overman, Larry E.
, p. 2186 - 2189 (2016)
The first total synthesis of a chromodorolide diterpenoid is described. The synthesis features a bimolecular radical addition/cyclization/fragmentation cascade that unites butenolide and trans-hydrindane fragments while fashioning two C-C bonds and stereoselectively forming three of the ten contiguous stereocenters of chromodorolide B.
Stereocontrolled total synthesis of (-)-kainic acid. Regio- and stereoselective lithiation of pyrrolidine ring with the (+)-sparteine surrogate
Morita, Yasuhiro,Tokuyama, Hidetoshi,Fukuyama, Tohru
, p. 4337 - 4340 (2005)
(Chemical Equation Presented) A stereocontrolled total synthesis of (-)-kainic acid is described. cis-3,4-Disubstituted pyrrolidine ring was constructed by [3 + 2] cycloaddition of azomethine ylide with chiral butenolide. The crucial introduction of carboxyl group at the C-2 position was executed by regio- and stereoselective lithiation of the pyrrolidine ring in the presence of a (+)-sparteine surrogate followed by trapping with carbon dioxide.
Synthesis and phytotoxicity of 4,5 functionalized tetrahydrofuran-2-ones
Resende, Gabriela C.,Alvarenga, Elson S.,Galindo, Juan C.G.,MacIas, Francisco A.
, p. 2266 - 2270 (2012)
In this work we report a versatile synthesis of fourteen γ-lactones all structurally related, nine of which are novel compounds, accomplished from the readily available furfural. The phytotoxic activity of the synthesized compounds was evaluated in vitro by the influence on the growth of wheat coleoptiles. The percentages of inhibition were mostly small and not statistically different from control after the third dilution (100 μmol L-1). In general, α,β-unsaturated lactones presented better activities than the saturated ones. The most active compounds presented 51, 68 and 76percent of inhibition in 1000 μmol L-1. The results indicate that regardless of saturation, the presence of the γ-lactone moiety is important for the bioactivity, but their presence has no implications with potency. ?2012 Sociedade Brasileira de Qui?mica.
Synthesis and pharmacological characterisation of arctigenin analogues as antagonists of AMPA and kainate receptors
Butts, Craig P.,Collingridge, Graham L.,Jane, David E.,Mallah, Shahida,Molnár, Elek,Re?nik, Lisa-Maria,Thatcher, Robert J.,Willis, Christine L.
supporting information, p. 9154 - 9162 (2021/11/16)
(-)-Arctigenin and a series of new analogues have been synthesised and then tested for their potential as AMPA and kainate receptor antagonists of human homomeric GluA1 and GluK2 receptors expressed in HEK293 cells using a Ca2+ influx assay. In general, these compounds showed antagonist activity at both receptors with greater activity evident at AMPARs. Schild analysis indicates that a spirocyclic analogue 6c acts as a non-competitive antagonist. Molecular docking studies in which 6c was docked into the X-ray crystal structure of the GluA2 tetramer suggest that (-)-arctigenin and its analogues bind in the transmembrane domain in a similar manner to the known AMPA receptor non-competitive antagonists GYKI53655 and the antiepileptic drug perampanel. The arctigenin derivatives described herein may serve as novel leads for the development of drugs for the treatment of epilepsy. This journal is
GRACILIN A AND CONGENERS AS IMMUNOSUPPRESSIVE AND NEUROPROTECTIVE AGENTS
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Page/Page column 51, (2019/10/01)
Gracilin A congeners and methods for their use as immunosuppressive and neuroprotective agents.
Catalytic asymmetric synthesis of geminal-dicarboxylates
Mistry, Nisha,Fletcher, Stephen P.
, p. 6307 - 6312 (2018/08/06)
Stereogenic acetals, spiroacetals and ketals are well-studied stereochemical features that bear two heteroatoms at a common carbon atom. These stereocenters are normally found in cyclic structures while linear (or acyclic) analogues bearing two heteroatoms are rare. Chiral geminal-dicarboxylates are illustrative, there is no current way to access this class of compounds while controlling the stereochemistry at the carbon center bound to two oxygen atoms. Here we report a rhodium-catalysed asymmetric carboxylation of ester-containing allylic bromides to form stereogenic carbon centers bearing two different carboxylates with high yields and enantioselectivities. The products, which are surprisingly stable to a variety of acidic and basic conditions, can be manipulated with no loss of enantiomeric purity as demonstrated by ring closing metathesis reactions to form chiral lactones, which have been extensively used as building blocks in asymmetric synthesis.
Enzymatic synthesis of optically active lactones via asymmetric bioreduction using ene-reductases from the old yellow enzyme family
Turrini, Nikolaus G.,Hall, Mélanie,Faber, Kurt
, p. 1861 - 1871 (2015/06/02)
In contrast to the widely studied asymmetric bioreduction of α,β-unsaturated carboxylic acid esters catalyzed by ene-reductases, the reaction applied to lactones remains unexplored. A broad set of ene-reductases was found to reduce various α-, β- and γ-substituted α,β-unsaturated butyrolactones to yield the corresponding saturated non-racemic lactones. Substitution patterns greatly influenced activities and stereoselectivities and lactone products were obtained in moderate to excellent yields; importantly, enzyme-based stereocontrol allowed access to both enantiomers in up to >99% ee. Chiral recognition of a distant γ-center led to kinetic resolution with remarkable enantioselectivities (E values up to 49). An unprecedented case of dynamic kinetic resolution was observed with 3-methyl-5-phenylfuran-2(5H)-one, whereby spontaneous racemization of the substrate furnished the product in up to 73% conversion and >99% ee and 96% de.
Catalytic aerobic oxidation of renewable furfural to maleic anhydride and furanone derivatives with their mechanistic studies
Lan, Jihong,Chen, Zhuqi,Lin, Jinchi,Yin, Guochuan
, p. 4351 - 4358 (2014/10/15)
Catalytic transformation of biomass-based furfural to value-added chemicals is an alternative route to the on-going fossil feedstock-based processes. This work describes catalytic aerobic oxidation of furfural to maleic anhydride, an important polymer starting material having a large market with H 5PV2Mo10O40 and Cu(CF 3SO3)2 catalysts. Under the optimized conditions, 54.0% yield of maleic anhydride can be achieved with about 7.5% yield of 5-acetoxyl-2(5H)-furanone formation. Notably, 5-acetoxyl-2(5H)-furanone is a highly value-added, biologically important intermediate that has been applied in pharmaceutical synthesis. The catalytic mechanism for furfural oxidation to maleic anhydride and 5-acetoxyl-2(5H)-furanone has been investigated in detail with identification of several key intermediates. the Partner Organisations 2014.
