Estudo visando à síntese total de morindaparvina A empregando química de benzino sob condições reacionais brandas
Data
2022-06-22
Autores
Souza, Vinícius Vieira de 
Orientadores
Raminelli, Cristiano
Tipo
Trabalho de conclusão de curso
Título da Revista
ISSN da Revista
Título de Volume
Resumo
A química de benzino tem encontrado diversas aplicações na síntese de produtos naturais e na preparação de materiais funcionais. Dentre os métodos para a geração de benzino e arinos, a reação entre 2-(trimetilsilil)aril trifluorometanossulfonatos e uma fonte de íons fluoreto tem ganhado destaque em química orgânica preparativa. Em conformidade, realizamos um estudo visando à síntese total da antraquinona morindaparvina A, um produto natural com significativa atividade antitumoral, empregando na etapa chave da síntese a reação de anelação de Hauser-Kraus entre 3-cianoftalida e TMS-aril trifluorometanossulfonato, promovida por uma fonte de íons fluoreto. No entanto, a reação de Hauser-Kraus não resultou na morindaparvina A.
Benzyne chemistry has found many applications in the synthesis of natural products and preparation of functional materials. Among the methods for the generation of benzyne and arynes, the reaction between 2-(trimethylsilyl)aryl trifluoromethanesulfonates and a source of fluoride ions has gained prominence in preparative organic chemistry. Accordingly, we carried out a study aiming at the total synthesis of anthraquinone morindaparvin A, a natural product with significant antitumor activity, employing in the key step of the synthesis the Hauser-Kraus annulation reaction between 3-cyanophthalide and TMS-aryl trifluoromethanesulfonate, promoted by a source of fluoride ions. However, the Hauser-Kraus reaction did not result in morindaparvin A.
Benzyne chemistry has found many applications in the synthesis of natural products and preparation of functional materials. Among the methods for the generation of benzyne and arynes, the reaction between 2-(trimethylsilyl)aryl trifluoromethanesulfonates and a source of fluoride ions has gained prominence in preparative organic chemistry. Accordingly, we carried out a study aiming at the total synthesis of anthraquinone morindaparvin A, a natural product with significant antitumor activity, employing in the key step of the synthesis the Hauser-Kraus annulation reaction between 3-cyanophthalide and TMS-aryl trifluoromethanesulfonate, promoted by a source of fluoride ions. However, the Hauser-Kraus reaction did not result in morindaparvin A.