168422-39-7Relevant academic research and scientific papers
Expeditious synthesis of the marine natural products prepolycitrin a and polycitrins a and b through heck arylations
Canto, Karen,Da Silva Ribeiro, Rodrigo,Biajoli, Andre F. P.,Correia, Carlos Roque D.
, p. 8004 - 8013 (2014/01/06)
New, efficient protocols for the syntheses of the marine natural products prepolycitrin A as well as polycitrins A and B were developed by employing the Heck-Matsuda arylation of maleic anhydride or dimethyl fumarate with aryldiazonium tetrafluoroborates. Both symmetrical and unsymmetrical 3,4-diarylmaleic anhydrides were easily and effectively prepared. Efficient bromination reactions that employed tribromoisocyanuric acid provided access to the polycitrin family of compounds. Under microwave irradiation in the presence of tyramine, the corresponding maleimides were obtained in high yields from the brominated 3,4-diarylmaleic anhydrides. This methodology provided for the concise synthesis of prepolycitrin A and the total syntheses of the marine alkaloids polycitrins A and B in overall yields of 37 and 47 % from maleic anhydride and dimethyl fumarate, respectively. The efficient and concise syntheses of the marine natural products prepolycitrin A as well as polycitrins A and B were accomplished by using a Heck-Matsuda arylation of maleic anhydride with aryldiazonium tetrafluoroborates. Polycitrins A and B were synthesized in overall yields of 37 and 47 %, respectively. Copyright
Heck arylation of maleic anhydrides using arenediazonium tetrafluoroborates: Synthesis of mono- and diarylated maleic anhydrides and of the marine alkaloids prepolycitrin A and Polycitrin A
Burtoloso, Antonio Carlos B.,Garcia, Ariel L. L.,Miranda, Karen C.,Correia, Carlos Roque D.
, p. 3145 - 3149 (2008/02/13)
The Heck arylation of maleic anhydrides using arenediazonium tetrafluoroborates was investigated. Symmetrical and unsymmetrical 3,4-diarylmaleic anhydrides, some of them showing interesting fluorescent properties, were prepared in one or two steps from ch
Biomimetic total synthesis of polycitrin A
Terpin, Andreas,Polborn, Kurt,Steglich, Wolfgang
, p. 9941 - 9946 (2007/10/02)
The synthesis of the marine alkaloid polycitrin A (1a) is described. The synthesis is based on the formation of 3,4-bisarylpyrrole-2,5-dicarboxylic acids from 3-arylpyruvic acids by oxidative coupling and consecutive pyrrole ring formation. The pyrrole di
