72031-58-4Relevant academic research and scientific papers
THE STRUCTURE AND SYNTHESIS OF FADYENOLIDE, A NEW BUTENOLIDE FROM PIPER FADYENII.
Pelter, Andrew,Al-Bayati, Redha,Haensel, Rudolf,Dinter, Hildegard,Burke, Basil
, p. 1545 - 1548 (1981)
The isolation, structure and synthesis of 5,6-Z- and E-fadyenolides, the simplest butenolides of the piperolide series, are reported.
A Rapid Entry to Diverse γ-Ylidenetetronate Derivatives through Regioselective Bromination of Tetronic Acid Derived γ-Lactones and Metal-Catalyzed Postfunctionalization
Chopin, Nicolas,Yanai, Hikaru,Iikawa, Shinya,Pilet, Guillaume,Bouillon, Jean-Philippe,Médebielle, Maurice
supporting information, p. 6259 - 6269 (2015/10/06)
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.
Regioselective bromination of tetronic acid-derived γ-lactones and metal-catalyzed post-functionalization: An efficient access to new γ-ylidenetetronate derivatives
Iikawa, Shinya,Chopin, Nicolas,Pilet, Guillaume,Bouillon, Jean-Philippe,Médebielle, Maurice
, p. 4577 - 4581 (2013/08/23)
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
Synthetic Routs to the Piperolides, Faydenolides, Epoxypiperolides, and Related Compounds
Pelter, Andrew,Al-Bayati, Redha I. H.,Ayoub, Miqdad T.,Lewis, Wynn,Pardasani, Pushpa,Hansel, Rudolf
, p. 717 - 742 (2007/10/02)
Syntheses of the piperolides, the faydenolides, epoxypiperolide, and related compounds are described. (+/-)-Narthogenin is also efficiently produced.
