Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2013, Issue 35, Pages 8004-8013Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201301108
Keywords
Total synthesis; Heterocycles; Alkaloids; Heck reaction; Palladium
Categories
Funding
- Sao Paulo Research Foundation (FAPESP) [2011/23832-6]
- Brazilian Research Council (CNPq)
- Coordination for the Improvement of Higher Education Level Personnel (CAPES)
- Fundacao de Amparo a Pesquisa do Estado de Sao Paulo (FAPESP) [11/23832-6] Funding Source: FAPESP
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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.
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