RESUMO
The total synthesis of atroviridin has been accomplished by a linear route involving the N-heterocyclic carbene (NHC)-catalyzed aroylation of the fluorobenzene derivative, Claisen cyclization of the O-propargylated benzophenones, and intramolecular 1,4-addition of the quinone intermediates. The result provides a viable route to xanthone natural products.
Assuntos
Produtos Biológicos/síntese química , Compostos Heterocíclicos/química , Metano/análogos & derivados , Xantonas/síntese química , Benzoquinonas/química , Produtos Biológicos/química , Catálise , Metano/química , Xantonas/químicaRESUMO
In N-heterocyclic carbene (NHCs) catalyzed nucleophilic substitution of fluorobenzenes, fluoro groups are replaced by aroyl groups, which are derived from aromatic aldehydes. 1,3,4,5-Tetramethylimidazol-2-ylidene is found to be an efficient catalyst. The catalyst loading can be reduced to 1 mol % without a significant decrease in the product yields. Polysubstituted benzophenones are synthesized from fluorobenzenes and benzaldehydes by the NHC-catalyzed aroylation.
