283614-77-7Relevant 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
First total synthesis of the alkaloid polycitrin B
Beccalli, Egle M.,Clerici, Francesca,Marchesini, Alessandro
, p. 2699 - 2702 (2007/10/03)
Starting from 3,5-dibromo-4-methoxy-phenylacetic acid methyl ester 2, a first total synthesis of the marine alkaloid polycitrin B is reported, based on the Pd catalyzed coupling reaction of the triflate 4 with the (4- methoxymethoxy-phenyl)tributylstannan
