21987-33-7Relevant academic research and scientific papers
Synthesis of novel ligands targeting phenazine biosynthesis proteins as a strategy for antibiotic intervention
Guttenberger, Nikolaus,Schlatzer, Thomas,Leypold, Mario,Tassoti, Sebastian,Breinbauer, Rolf
, p. 847 - 856 (2018)
Abstract: In this contribution, we report synthetic strategies towards potential ligands for the study of binding differences between PhzE, the first enzyme in the biosynthesis of phenazines, and the related enzyme anthranilate synthase. The ligands were
Synthetic approach to seco-tetracenomycin natural products saccharothrixone A–C
Chinta, Bhavani Shankar,Sanapa, Harikrishna,Vasikarla, Kamala Prasad,Baire, Beeraiah
supporting information, p. 1970 - 1973 (2018/04/20)
Design and development of first synthetic approach to the functionalized tetracyclic framework of structurally novel seco-tetracenomycin natural products saccharothrixones A–C has been reported. A thermal dehydro Diels-Alder reaction of an arenyne-alkyne
Diels-Alder and Dehydration Reactions of Biomass-Derived Furan and Acrylic Acid for the Synthesis of Benzoic Acid
Mahmoud, Eyas,Yu, Jingye,Gorte, Raymond J.,Lobo, Raul F.
, p. 6946 - 6955 (2015/11/23)
Routes to benzoic acid starting from furan-obtained from hemicellulose in high yield-and methyl acrylate are reported. These routes involve Diels-Alder and dehydration reactions of furan and acrylic acid (or methyl acrylate) in a two-step reaction protocol that minimizes side reactions. The Diels-Alder reaction of furan and methyl acrylate (or acrylic acid) was run at 298 K and was catalyzed by Lewis acidic (Hf-, Zr-, and Sn-Beta) zeolite catalysts, and achieving a high turnover frequency (～2 h-1) and no side reactions were observed. The oxanorbornene product was dehydrated at low temperatures (298 to 353 K) in mixtures of methanesulfonic acid and acetic anhydride in 96% yield. This is compared to an only 1.7% yield of methyl benzoate obtained for the dehydration of the oxanorbornene in neat methanesulfonic acid. The effect of oxanorbornene concentration and stereochemistry was found not to decrease the yield of aromatics, while dehydration of the carboxylic acid form of the oxanorbornene led to a decrease in selectivity to 43% at complete conversion in mixtures of methanesulfonic acid and acetic anhydride. This reaction sequence could be an important entry point for selectively directing high-yield, hemicellulose-derived furans to aromatic products used in the existing chemical process industry.
Regiodivergent addition of phenols to allylic oxides: Control of 1,2- and 1,4-additions for cyclitol synthesis
Moschitto, Matthew J.,Vaccarello, David N.,Lewis, Chad A.
supporting information, p. 2142 - 2145 (2015/02/19)
Control of 1,2- and 1,4-addition of substituted phenols to allylic oxides is achieved by intercepting palladium π-allyl complexes. The interconversion of palladium complexes results in the total synthesis of MK7607, cyathiformine B type, streptol, and a new cyclitol.
Niobium(V) chloride as catalyst in diels-alder reaction of furan ring
Santos, Deborah A. Dos,Rodrigues, Ludmila R.,Arpini, Bruno H.,Lacerda Jr., Valdemar,Greco, Sandro J.,Santos, Reginaldo B. Dos,Neto, A?lvaro C.,Roma?oa, Wanderson,De Castro, Eustaquio V.R.
, p. 882 - 886 (2014/06/24)
According to the relevant literature, the Diels-Alder reaction of furan without a catalyst can last several weeks and shows a low yield due to the diene's low reactivity. The use of Lewis acid catalysts or high pressures is described as an effective method for improving the reaction yields. This paper describes our recent study on the use of niobium pentachloride as the catalyst in Diels-Alder reactions between furan and several reactive dienophiles, among which methyl acrylate showed good yields, especially at lower temperatures. Other dienophiles have shown lower yields because of problems such as byproduct formation and the high reversibility of the reaction.
Norbornenes in inverse electron-demand diels-alder reactions
Vrabel, Milan,Koelle, Patrick,Brunner, Korbinian M.,Gattner, Michael J.,Lopez-Carrillo, Veronica,De Vivie-Riedle, Regina,Carell, Thomas
supporting information, p. 13309 - 13312 (2013/10/08)
Significant differences in the reactivity of norbornene derivatives in the inverse electron-demand Diels-Alder reaction with tetrazines were revealed by kinetic studies. Substantial rate enhancement for the exo norbornene isomers was observed (see scheme). Quantum-chemical calculations were used to rationalize and support the observed experimental data. Copyright
A large-molecular-weight polyanion, synthesized via ring-opening metathesis polymerization, as a lubricant for human articular cartilage
Wathier, Michel,Lakin, Benjamin A.,Bansal, Prashant N.,Stoddart, Stephanie S.,Snyder, Brian D.,Grinstaff, Mark W.
supporting information, p. 4930 - 4933 (2013/05/22)
A large-molecular-weight polyanion is found to possess lubricating properties for cartilage. The polyanion, sodium poly(7-oxanorbornene-2- carboxylate), is synthesized by ring-opening metathesis polymerization of methyl 5-oxanorbornene-2-carboxylate. When dissolved in aqueous solution and applied to the surface of human cartilage it reduces the friction at the interface and acts as a lubricant. Its performance is similar to that of synovial fluid and superior to those of saline and Synvisc in an ex vivo human cartilage plug-on-plug model. The polymer is also not readily degraded by hyaluronidase or cytotoxic to human chondrocytes in vitro. As such, this polymer is a new type of viscosupplement, and the results provide insight into the design requirements for synthesizing highly efficacious synthetic biolubricants.
Synthesis of carba analogs of 6-O-(benzyl)-d-allal- and -d-galactal-derived allyl epoxides and evaluation of the regio- and stereoselective behavior in nucleophilic addition reactions
Di Bussolo, Valeria,Frau, Ileana,Checchia, Lorenzo,Favero, Lucilla,Pineschi, Mauro,Uccello-Barretta, Gloria,Balzano, Federica,Roselli, Graziella,Renzi, Gabriele,Crotti, Paolo
scheme or table, p. 4696 - 4709 (2011/06/27)
The new racemic diastereoisomeric epoxides 6α and 6β, the carba analogs of the corresponding d-galactal- and d-allal-derived allyl epoxides have been synthesized and their regio- and stereoselective behavior examined in addition reactions with model O-, C-, N-, and S-nucleophiles. The results have indicated that epoxide 6β has a pronounced tendency toward anti-1,2-addition, whereas epoxide 6α shows interesting levels of syn- and/or anti-1,4-addition processes. A chiral recognition process found with epoxide 6β, turned out to be consistently reduced in epoxide 6α. All the results have been rationalized on the basis of conformational, steric, and stereoelectronic effects.
Acidic polysaccharide mimics via ring-opening metathesis polymerization
Wathier, Michel,Stoddart, Stephanie S.,Sheehy, Matthew J.,Grinstaff, Mark W.
supporting information; experimental part, p. 15887 - 15889 (2011/01/11)
An efficient and general synthetic strategy for the preparation of high-molecular-weight hydrophilic polymers bearing both carboxylic acid and hydroxyl pendant groups is described. Specifically, poly(5,6- dihydroxyoxanorbornane carboxylic acid) with molecular weight ranging from ～100 000 to 5 000 000 g/mol was prepared by ring-opening metathesis polymerization of methyl 5-oxanorbornene-2-carboxylate in the presence of Grubbs catalyst II and subsequently modified to tune the hydrophobic/hydrophilic properties by the introduction of either hydroxyl or carboxylic acid functionalities. These polymers mimic the natural acidic polysaccharide alginate and form hydrogels with polylysine. These polymers belong to a class of carbohydrate-like polymers, which are of interest for investigating the relationships between chemical structure and rheological properties as well as for providing new synthetic polysaccharide substitutes for applications in the biotechnology and pharmaceutical industries.
Endo selective Diels-Alder reactions of furan in ionic liquids
Hemeon, Ivan,DeAmicis, Carolyn,Jenkins, Hilary,Scammells, Peter,Singer, Robert D.
, p. 1815 - 1818 (2007/10/03)
Diels-Alder reactions of the heteroaromatic diene furan proceed with enhanced isolated yields and reversal of endolexo selectivity (2:1 endo vs exo) in the ionic liquids [bmim]BF4 and [bmim]PF6 compared to conventional methods. The p
