Estudos visando sínteses totais de substâncias bioativas
Data
2020-03-06
Autores
Perecim, Givago Prado 
Orientadores
Raminelli, Cristiano
Tipo
Tese de doutorado
Título da Revista
ISSN da Revista
Título de Volume
Resumo
A química de benzino tem encontrado aplicações em química orgânica, incluindo sínteses totais de produtos naturais e preparações de materiais funcionais. Neste sentido, 2-(trimetilsilil)aril trifluorometanossulfonatos surgem como uma alternativa importante para a formação de benzino e derivados, sob condições reacionais brandas, ampliando o escopo de aplicações da química de benzino em química orgânica preparativa. Dentro deste contexto, realizamos estudos visando as sínteses totais de substâncias bioativas, a saber: cloridrato de (±)-apomorfina (protótipo aporfinoide); (S)-nuciferina e (R)- nuciferina (alcaloides aporfínicos), bem como morindaparvina A, 1,2- dimetoxiantraquinona, 1-metoxiantraquinona, 2,3-dimetilantraquinona e 2,3- difluorantraquinona (antraquinonas não quirais), com potenciais farmacológicos de interesse, empregando 2-(trimetilsilil)aril triflatos nas correspondentes etapas chaves, sob condições reacionais brandas.
Benzene chemistry has found applications in organic chemistry, including total natural product syntheses and functional material preparations. In this sense, 2-(trimethylsilyl)aryl trifluoromethanesulfonates emerge as an important alternative for the formation of benzene and derivatives, under mild reaction conditions, expanding the scope of applications of benzene chemistry in preparative organic chemistry. Within this context, we carried out studies aiming at the total synthesis of bioactive substances, namely: (±)-apomorphine hydrochloride (aporphinoid prototype); (S)-nuciferin and (R)-nuciferin (aporphine alkaloids), as well as morindaparvin A, 1,2-dimethoxyanthraquinone, 1-methoxyanthraquinone, 2,3-dimethylanthraquinone and 2,3-difluoroanthraquinone (non-chiral anthraquinones), with potential pharmacological studies of interest, employing 2-(trimethylsilyl)aryl triflates in the corresponding key steps, under mild reaction conditions.
Benzene chemistry has found applications in organic chemistry, including total natural product syntheses and functional material preparations. In this sense, 2-(trimethylsilyl)aryl trifluoromethanesulfonates emerge as an important alternative for the formation of benzene and derivatives, under mild reaction conditions, expanding the scope of applications of benzene chemistry in preparative organic chemistry. Within this context, we carried out studies aiming at the total synthesis of bioactive substances, namely: (±)-apomorphine hydrochloride (aporphinoid prototype); (S)-nuciferin and (R)-nuciferin (aporphine alkaloids), as well as morindaparvin A, 1,2-dimethoxyanthraquinone, 1-methoxyanthraquinone, 2,3-dimethylanthraquinone and 2,3-difluoroanthraquinone (non-chiral anthraquinones), with potential pharmacological studies of interest, employing 2-(trimethylsilyl)aryl triflates in the corresponding key steps, under mild reaction conditions.