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Synthesis of bioactive complex structures via valorisation of bio renewable resources
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Furan-based compounds, such as furfural and 5-hydroxymethylfurfural, obtained through the dehydration of pentoses and hexoses from lignocellulosic biomass, are important building blocks in the production of various chemicals. The reactivity of these furanic platforms has been explored to create new chemical entities with high complexity and diversity.
This thesis addresses the synthesis of trans-4,5-diamino-cyclopent-2-enones (DCP) from furfural, with a focus on developing an asymmetric methodology in order to produce chiral bifunctionalized cyclopentenones. The formation of chiral centers in these molecules allows for higher molecular complexity and access to a wider chemical space. The potential application of regioselective δ-lactone-fused cyclopentenones (LCP) and trans-4,5-diaminocyclopent-2-enones (DCP) as antimalarial compounds was also studied. Promising IC50 values were obtained for various DCP derivatives, highlighting their potential despite the promiscuity commonly associated with the Michael acceptor of the cyclopentenone core.
The synthesis of nitrogen-containing compounds plays a crucial role in the pharmaceutical industry. Sustainable methodologies for the synthesis of 3-acetamido-5-acetylfuran (3A5AF), a promising bio-renewable building block, from chitin (a nitrogen-rich biopolymer), were developed, aiming to overcome limitations of previously reported methods. To optimize the synthetic process, a machine learning-assisted approach was employed, resulting in improved yields. The direct use of 3A5AF as a diene in Diels-Alder (DA) cycloaddition reactions was investigated, leading to the synthesis of 7- oxanorbornenes. The incorporation of renewable nitrogen into these compounds was highlighted to produce polymer materials, fine chemicals, and commodity aromatics.
Furthermore, this work explored the formation of aminals from aromatic aldehydes including furfural and HMF under mild conditions. These aminals found utility as aldehyde protection groups, scavengers of potential genotoxic impurities, and stimuli-responsive release systems.
Overall, this thesis provides valuable insights into the sustainable synthesis of diverse and complex chemical compounds from biomass-derived furanic platforms, offering new possibilities for the utilization of renewable resources in chemical synthesis and pharmaceutical applications.
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Palavras-chave
Sustentabilidade Biomassa Furanos Ciclopentenonas Aminais Sustainability Biomass Furfurals Cyclopentenones Aminals