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Doctoral Thesis
DOI
10.11606/T.46.2018.tde-12042018-094752
Document
Author
Full name
Eloisa Eriko Ishikawa
E-mail
Institute/School/College
Knowledge Area
Date of Defense
Published
São Paulo, 2017
Supervisor
Committee
Baader, Josef Wilhelm (President)
Cunha, Silvio do Desterro
Marzorati, Liliana
Omori, Alvaro Takeo
Viertler, Hans
Title in Portuguese
Estudos visando a síntese total assimétrica do populeno D e alquilação regiosseletiva de N-aril-2-aminopirimidinas catalisada por rutênio(II)
Keywords in Portuguese
Ciclização de Prins
Funcionalização C-H
Iodo
Populeno D
Rutênio
Síntese total assimétrica
Abstract in Portuguese
São apresentados nesta tese os resultados dos estudos visando a síntese total assimétrica do populeno D, um produto natural extraído do troco da árvore Thespesia populnea. A proposta sintética era obter a molécula alvo em 14 etapas, entretanto, não foi possível finalizar a síntese. Foi obtido o último intermediário da síntese em 13 etapas em um rendimento global de 8%, a partir do L-lactato de etila, comercialmente disponível. A rota sintética proposta tem como etapa chave uma reação de ciclização de Prins catalisada por iodo molecular. Tal metodologia foi utilizada para sintetizar quatro análogos do populeno D, compostos inéditos que foram caracterizados e enviados para ensaios de atividade biológica. Dois destes quatro compostos apresentaram bons resultados contra linhagens celulares do ovário com fenótipo de resistência a múltiplos fármacos. Apresenta-se também uma metodologia de meta-alquilação de N-aril-2- aminopirimidinas com haletos secundários catalisada por rutênio. No total, foram obtidos vinte compostos inéditos que foram completamente caracterizados.
Title in English
Studies towards asymmetric total synthesis of populene D. Ruthenium-catalyzed site-selective alkylations of N-aryl-2-aminopyrimidines
Keywords in English
Asymmetric total synthesis
C-H functionalization
Iodine
Populene D
Prins cyclization
Ruthenium
Abstract in English
Studies aiming the asymmetric total synthesis of populene D are presented in this thesis. Populene D is a natural product extracted from Thespesia populnea tree trunk. Synthetic proposal for the target molecule comprised 14 steps, however, total synthesis was not achieved. Last intermediate of the proposed route was obtained, in 13 steps and 8% global yield, starting from commercially available ethyl L-lactate. An iodine-catalyzed Prins cyclization reaction is the key step of proposed synthesis. This methodology was applied to synthesize four analogues of populene D, all unknown compounds which were fully characterized, and submitted to biological activity tests. Among these four compounds, two of them have shown good results against ovary cell lines with with multidrug resistance phenotype. A new protocol of ruthenium-catalyzed site-selective alkylation of N-aryl-2- aminopyrimidines is also presented in this thesis. 20 unknown compounds were obtained using this protocol and they were fully characterized as well.
 
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Publishing Date
2018-04-26
 
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