81189-55-1Relevant academic research and scientific papers
Parallel synthesis: A new approach for developing analytical internal standards. Application to the analysis of patulin by gas chromatography-mass spectrometry
Llovera, Montserrat,Balcells, Merce,Torres, Merce,Canela, Ramon
, p. 6643 - 6648 (2005)
The polymer-assisted reaction of 4-(hydroxymethyl)furan-2(5H)-one (4HM2F) with 21 carboxylic acids using polystyrene-carbodiimide (PS-carbodiimide) yielded an ester library. Four of the esters, (5-oxo-2,5-dihydrofuran-3-yl) methyl acetate (IS-1), (5-oxo-2
Application of the palladium-catalysed norbornene-assisted catellani reaction towards the total synthesis of (+)-linoxepin and isolinoxepin
Qureshi, Zafar,Weinstabl, Harald,Suhartono, Marcel,Liu, Hongqiang,Thesmar, Pierre,Lautens, Mark
, p. 4053 - 4069 (2014/07/08)
Our ongoing effort towards the development of highly selective transition-metal-catalysed C-H activation processes has led to the expansion of the Catellani reaction. In a Pd0/PdII/Pd IV-catalysed domino reaction, an aryl iodide, alkyl iodide and tert-butyl acrylate were combined to synthesize the carbon framework of the novel lignan (+)-linoxepin. The enantioselective synthesis highlights the work accomplished in our group and provides an excellent procedure for the reliable and scalable synthesis of architecturally complex scaffolds. This report outlines the synthetic approaches towards this interesting class of biologically active molecules. After the key Catellani/Heck reaction, our synthesis features a Leimeux-Johnson oxidation and a titanium tetrachloride mediated aldol condensation. Finally, a tuneable Mizoroki-Heck reaction was performed to furnish not only the natural product (+)-linoxepin but also its isoform, which we have named isolinoxepin. The enantioselective total synthesis of the natural product (+)-linoxepin has been accomplished in eight steps starting from commercial materials. The key Pd-catalysed Catellani step served to combine aryl iodide, alkyl iodide and tert-butyl acrylate in a domino sequence. By tuning the final Heck reaction, both the natural product and its structural isomer were synthesized. Copyright
Gas-phase fragmentation of γ-lactone derivatives by electrospray ionization tandem mass spectrometry
Crotti, Antonio E. M.,Bronze-Uhle, Erika S.,Nascimento, Paulo G. B. D.,Donate, Paulo M.,Galembeck, Sergio E.,Vessecchi, Ricardo,Lopes, Norberto P.
experimental part, p. 1733 - 1741 (2010/08/04)
Fragmentation reactions of β-hydroxymethyl-, β-acetoxymethyl- and β-benzyloxymethyl-butenolides and the corresponding γ-butyrolactones were investigated by electrospray ionization tandem mass spectrometry (ESI-MS/MS) using collision-induced dissociation (CID). This study revealed that loss of H2O [M+H-18]+ is the main fragmentation process for β-hydroxymethylbutenolide (1) and β-hydroxymethyl-γ- butyrolactone (2). Loss of ketene ([M+H-42]+) is the major fragmentation process for protonated β-acetoxymethyl-γ-butyrolactone (4), but not for β-acetoxymethylbutenolide (3). The benzyl cation (m/z 91) is the major ion in the ESI-MS/MS spectra of β-benzyloxymethylbutenolide (5) and β-benzyloxymethyl-γ-butyrolactone (6). The different side chain at the β-position and the double bond presence afforded some product ions that can be important for the structural identification of each compound. The energetic aspects involved in the protonation and gas-phase fragmentation processes were interpreted on the basis of thermochemical data obtained by computational quantum chemistry. Copyright
A facile chemoenzymatic approach to natural cytotoxic ellipsoidone A and natural ellipsoidone B
Gogoi, Sanjib,Argade, Narshinha P.
, p. 2715 - 2720 (2007/10/03)
Starting from citraconic anhydride (3) a facile four-step synthesis of deoxyellipsoidone 8 has been reported with 37% overall yield. An elegant six-step access to naturally occurring cytotoxic ellipsoidone A (1) and ellipsoidone B (2) has been reported with good overall yields, via the conversion of itaconic anhydride (9) to the acetoxymethylmaleic anhydride (11), regioselective sodium borohydride reduction of anhydride 11 to acetoxymethylbutyrolactone 12, Knoevenagel condensation of lactone 12 with 5-methylfurfural, selenium dioxide induced oxidation of the formed butenolide 13 and an Amano PS catalyzed deacylation of the formed diacetoxybutenolide 14 as a pathway.
From tetronic acid and furfural to C(4)-halogenated, vinylated and formylated furan-2(5H)-ones and their 5-alkoxy derivatives
Lattmann,Hoffmann
, p. 155 - 163 (2007/10/03)
Tetronic acid and furfural have been elaborated into the title compounds. Palladium-catalyzed cross coupling with vinylstannanes and controlled ozonolysis followed by anhydrous workup are key reactions.
Asymmetric Reduction of 3-Hydroxymethylbutenolide Derivatives by Bakers' Yeast: A New Approach to the Synthesis of Factor-I
Takabe, Kunihiko,Tanaka, Masaya,Sugimoto, Masahisa,Yamada, Takashi,Yoda, Hidemi
, p. 1385 - 1386 (2007/10/02)
Bakers' yeast reduction of 3-benzyloxymethylbutenolide gave (S)-3-benzyloxymethylbutanolide, and its transformation to Factor-I, the autoregulator of Streptomyces viridocchromogenes, was examined.
Potentially Mutagenic, Chlorine-Substituted 2(5H)-Furanones: Studies of Their Synthesis and NMR Properties
LaLonde, Robert T.,Perakyla, Hannu,Hayes, Michael P.
, p. 2847 - 2855 (2007/10/02)
The mutagen 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone (MX), 1, and seven analogues of it were synthesized from 4-(hydroxymethyl)-2(5H)-furanone, 2.This investigation was untertaken to learn if 2 would serve as a versatile starting point for the preparation of MX analogues required for structure/activity studies of genotoxicity.Compound 2 was treated with thionyl chloride-pyridine to develop the C-4 chloromethyl group.Oxidation of 2 with pyridinium chlorochromate to the aldehyde, followed by treatment of the latter with phosphorus pentachloride, developed the C-4 dichloromethyl group.Thereafter, when attachment of chlorine at C-3 was desired, the aluminum chloride promoted chlorine addition to the C-3-C-4 double bond followed by the triethylamine-promoted elimination of hydrogen chloride resulted in the required 3-chloro-4-(chloromethyl) or 4-(dichloromethyl)-5-desoxy analogues of MX.Hydroxylation at C-5 was achieved in two steps, involving first bromine substitution employing NBS under free radical conditions followed by metal ion assisted hydrolysis of the bromide in aqueous acetone.Special regard was paid to the characterization of MX and its analogues by assessing the values of 13C NMR chemical shift, the consistency of substitution effects, and the occurrence and magnitude of direct and long-range couplings in the spectra of these compounds.
