17559-81-8Relevant articles and documents
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de Wit,J.,Wynberg,H.
, p. 1379 - 1391 (1973)
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Oxidations catalysed by rhenium(V) oxo species 1. Conversion of furans to enediones using methyltrioxorhenium and urea hydrogen peroxide
Finlay, James,McKervey, M. Anthony,Gunaratne, H. Q. Nimal
, p. 5651 - 5654 (1998)
Methyltrioxorhenium is an efficient catalyst for the oxidative ring opening of several substituted furans to enediones using urea hydrogen peroxide.
Mo(CO)6-catalyzed oxidation of furan derivatives to E- and Z-enediones by cumyl hydroperoxide
Massa, Antonio,Acocella, Maria Rosaria,De Rosa, Margherita,Soriente, Annunziata,Villano, Rosaria,Scettri, Arrigo
, p. 835 - 837 (2003)
E- and Z-Enediones are easily accessible by controlled oxidation of 2,5-disubstituted furans with Mo(CO)6/cumyl hydroperoxide system. The use of t-butyl hydroperoxide, as oxygen donor, leads to the formation of 2H-pyran-3(6H)-one derivatives.
Enedione-Functionalized Macrocycles via Oxidative Ring Opening of Furans
Williams, Peter D.,LeGoff, Eugene
, p. 4143 - 4147 (1981)
A series of novel polyketo macrocycles was synthesized by oxidative ring opening of the cyclic furan-acetone tetramer 1 and hexamer 2.Reaction of 1 with bromine in acetic acid-water gave the bis(trans-enedione) 3.The use of m-chloroperoxybenzoic acid allowed for the controlled oxidation of 1, giving ring-opened products with the cis-enedione configuration.Reaction using 4.2 equiv of the peracid with 1 gave the tetra-ring-opened octaketone 5 in good yield.Analogously, the hexamer 2, in the reaction with 6.3 equiv of peracid, gave the all-cis unsaturated dodecaketone6.By varying the stoichiometry of the peracid in its reaction with 1, the tri-ring-opened and the two regioisomeric di-ring-opened cis-enediones 7-9, respectively, were isolated.Acid-catalyzed isomerization of 8 and 9 gave the corresponding trans-enediones 3 and 10, respectively, and the structures of these cis and trans isomers were correlated by reduction of the enedione double bonds either by using zinc in acetic acid or by catalytic hydrogenation.The X-ray structures and UV-vis spectra of 3 and 5 are discussed.
INTRAMOLECULAR REARRANGEMENT OF THIOOZONIDES: SULFINE FORMATION WITHOUT SULFUR ATOM SCRAMBLING, A DOUBLE ISOTOPE CROSSOVER STUDY
Matturro, Michael G.,Reynolds, Robert P.
, p. 4981 - 4984 (1987)
Decomposition of a mixture of 34S and deuterium labeled thioozonides prepared by photooxidation of dimethylthiophenes in CDCl3 has shown that intramolecular rearrangement to thioketone S-oxide, a stable 1,3-dipole, proceeds cleanly without sulfur atom scrambling in the presence of sulfur allotropes.
MAGNESUIM MONOPEROXYPHTHALATE: A NEW REAGENT FOR THE OXIDATIVE RING OPENING OF FURANS TO CIS-ENEDIONES
Dominguez, Carmen,Csaky, Aurelio G.,Plumet, Joaquin
, p. 7669 - 7670 (1990)
Ring opening of furans can be accomplished with the title reagent to afford cis-enediones stereospecifically, with great advantages over the hazardous MCPBA.
Stereoselective Synthesis of cis-2-Ene-1,4-diones via Aerobic Oxidation of Substituted Furans Catalyzed by ABNO/HNO3
Yang, Liqun,Wang, Jingyang,Wang, Yue,Li, Xiaotong,Liu, Wei,Zhang, Zhaoguo,Xie, Xiaomin
supporting information, p. 14311 - 14320 (2021/10/25)
We report a highly efficient and selective catalytic system, ABNO (9-azabicyclo-[3.3.1]nonane N-oxyl)/HNO3, for the aerobic oxidation of substituted furans to cis-2-ene-1,4-diones under mild reaction conditions using oxygen as the oxidant. The catalyst system is amenable to various substituted (mon-, di-, and tri-) furans and tolerates diverse functional groups, including cyano, nitro, naphthyl, ketone, ester, heterocycle, and even formyl groups. Based on the control and 18O-labeling experiments, the possible mechanism of the oxidation is proposed.
Highly Reactive and Tracelessly Cleavable Cysteine-Specific Modification of Proteins via 4-Substituted Cyclopentenone
Yu, Jian,Yang, Xiaoyue,Sun, Yang,Yin, Zheng
supporting information, p. 11598 - 11602 (2018/09/10)
A rapid and cysteine-specific modification of proteins using 4-substituted cyclopentenone via a Michael addition tandem elimination reaction was developed. Compared to the classical method, this reaction featured fast kinetics with a stable product. More importantly, this conjugation could be tracelessly removed by exchange with a Michael addition donor. The conjugation and regeneration process not only exhibited little change to the structures or conformations of the proteins but also exhibited little disturbance to their biological functions, such as their enzymatic activities.
Total synthesis of paracaseolide A
Guney, Tezcan,Kraus, George A.
supporting information, p. 613 - 615 (2013/04/23)
The total synthesis of paracaseolide A, a valuable cell-cycle progression inhibitor, was accomplished in 8 steps from known compounds, with 6.6% overall yield. The synthetic strategy creates strong potential for diversification.
