- A Rapid Entry to Diverse γ-Ylidenetetronate Derivatives through Regioselective Bromination of Tetronic Acid Derived γ-Lactones and Metal-Catalyzed Postfunctionalization
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The synthesis of a series of diverse methyl and benzyl γ-ylidenetetronate derivatives was accomplished through the condensation of methyl and benzyl tetronates with (hetero)aryl aldehydes in a new two- or three-step aldolisation/dehydration sequence. The bromination of methyl and benzyl γ-ylidenetetronates occurred under mild conditions to provide the corresponding C-3-brominated γ-unsaturated lactones. Di- and tribrominated γ-lactones were prepared under slightly different conditions. Some brominated materials were employed in representative Stille, Suzuki-Miyaura, and Sonogashira cross-coupling reactions to yield functionalized methyl and benzyl γ-ylidenetetronate derivatives. Compounds that resulted from the Sonogashira cross-coupling reactions were desilylated and converted into 1,2,3-triazole derivatives through a copper(I)-catalyzed 1,3-dipolar cycloaddition reaction with benzyl azide.
- Chopin, Nicolas,Yanai, Hikaru,Iikawa, Shinya,Pilet, Guillaume,Bouillon, Jean-Philippe,Médebielle, Maurice
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supporting information
p. 6259 - 6269
(2015/10/06)
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- Regioselective bromination of tetronic acid-derived γ-lactones and metal-catalyzed post-functionalization: An efficient access to new γ-ylidenetetronate derivatives
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The synthesis of several methyl and benzyl γ-ylidenetetronates was accomplished and the bromination reactions of these derivatives, using bromine or N-bromosuccinimide (NBS), were found to occur under mild conditions. Several new brominated γ-unsaturated
- Iikawa, Shinya,Chopin, Nicolas,Pilet, Guillaume,Bouillon, Jean-Philippe,Médebielle, Maurice
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p. 4577 - 4581
(2013/08/23)
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- Highly regioselective 3-hydroxyalkylations of boron 4-methoxy-2-furanolates: A new entry to 5-unsubstituted and 5-monosubstituted 3-acyl-4-o-methyl tetronates
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Boron 4-methoxy-2-furanolates generated in situ from 5-unsubstituted and 5-monosubstituted 4-O-methyl tetronates undergo highly regioselective 3-hydroxyalkylations with aldehydes to give 5-unsubstituted and 5-monosubstituted 3-acyl-4-O-methyl tetronates, respectively, in good overall yields after oxidation of the intermediate alcohols with 2-iodoxybenzoic acid.
- Paintner,Allmendinger,Bauschke
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p. 2113 - 2118
(2007/10/03)
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- Process for the production of threo-4-alkoxy-5- (arylhydroxymethyl)-2(5H)-furanones
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Threo-4-alkoxy-5-(arylhydroxymethyl)-2(5H)-furanones are obtained by condensation of 4-alkoxy-2(5H)-furanones with benzaldehydes in the presence of lithium hydroxide without contamination by the corresponding erythro stereoisomers. The condensation is pre
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- Synthetic Routs to the Piperolides, Faydenolides, Epoxypiperolides, and Related Compounds
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Syntheses of the piperolides, the faydenolides, epoxypiperolide, and related compounds are described. (+/-)-Narthogenin is also efficiently produced.
- Pelter, Andrew,Al-Bayati, Redha I. H.,Ayoub, Miqdad T.,Lewis, Wynn,Pardasani, Pushpa,Hansel, Rudolf
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p. 717 - 742
(2007/10/02)
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- 2-TRIMETHYLSILYLOXY-4-METHOXYFURAN: AN EXCELLENT SYNTHON FOR THE PRODUCTION OF 5-SUBSTITUTED TETRONATES (4-METHOXYBUTENOLIDES).
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The preparation of 2-trimethylsilyloxy-4-methoxyfuran (6) is described.Under the influence of Lewis acids, this compound is substituted by a wide variety of reagents in a regiospecific fashion at C-5 to give substituted methyl tetronates.Its utility is ex
- Pelter, Andrew,Al-Bayati, Redha,Lewis, Winne
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p. 353 - 356
(2007/10/02)
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