Estudo visando à síntese total da (S)-nuciferina

Detalhes bibliográficos
Ano de defesa: 2018
Autor(a) principal: Silva, Tamiris Reissa Cipriano da [UNIFESP]
Orientador(a): Não Informado pela instituição
Banca de defesa: Não Informado pela instituição
Tipo de documento: Dissertação
Tipo de acesso: Acesso aberto
Idioma: por
Instituição de defesa: Universidade Federal de São Paulo
Programa de Pós-Graduação: Não Informado pela instituição
Departamento: Não Informado pela instituição
País: Não Informado pela instituição
Palavras-chave em Português:
Link de acesso: https://sucupira.capes.gov.br/sucupira/public/consultas/coleta/trabalhoConclusao/viewTrabalhoConclusao.jsf?popup=true&id_trabalho=6344555
https://repositorio.unifesp.br/handle/11600/52824
Resumo: Considering bioactive natural products, aporphine alkaloids compose an important class of compounds that acts as dopamine receptor ligands. In addition, some of these alkaloids, among which we stand out (±)-nuciferine, have presented selective blockade of serotonin 5-HT2A receptor, which in therapeutic terms is related to various disorders, including schizophrenia, insomnia, and ischemic heart disease. Furthermore, aporphine alkaloids have other important biological activities, including, for example, anti-HIV and antineoplastic activities. Having in mind the great biological importance of this class of natural products, we have worked in the enantioselective total synthesis of (S)-nuciferine, through a novel approach to obtain chiral aporphine alkaloids, employing in key steps of the synthesis [4 + 2] cycloaddition reaction followed by hydrogen migration, via benzyne chemistry under mild conditions, and enantioselective hydrogenation reaction, using hydrogen in the presence of catalytic amount of noble metal complex (Ru, Rh, and Ir) containing chiral ligand (monodentate and bidentate). Although (S)-nuciferine has not been achieved, the study of enantioselective reduction reactions afforded relevant information about the stability of dehydroaporphine skeletons and allowed the expansion by searching of better conditions to complete the synthesis in the future.