PPG - Biologia Química

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https://hdl.handle.net/11600/61107

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Navegando PPG - Biologia Química por Palavras-chave "(+)-Bernumidine"

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    Síntese total da (+)-bernumidina e estudos visando à síntese total da (-)-Lirinidina
    (Universidade Federal de São Paulo, 2018-09-14) Correa, Bianca Kobal [UNIFESP]; Raminelli, Cristiano [UNIFESP]; Universidade Federal de São Paulo (UNIFESP)
    Chemoenzymatic dynamic kinetic resolution (DKR) constitutes a convenient and efficient approach to access enantiomerically enriched alcohols and amines. However, chemoenzymatic DKR of secondary amines can be considered challenging processes and, currently, there is a limited number of chemoenzymatic dynamic kinetic resolutions involving secondary amines reported in the literature. Accordingly, in this work we accomplished the total synthesis of the benzylisoquinoline alkaloid (+)-bernumidine, which has potential as ligand for the μ opioid receptor, employing a chemoenzymatic dynamic kinetic resolution. In addition, we evaluate the chemoenzymatic DKR using the compound (±)-nornuciferine aiming to obtain the alkaloid (-)-lirinidine, which acts as a serotonergic receptor antagonist and exhibits a significant inhibition of platelet aggregation. The total synthesis of (+)-bernumidine was performed in 6 steps with a 39% overall yield and involved a known chemoenzymatic dynamic kinetic resolution. The total synthesis of (-)-lyrinidine could not be completed employing chemoenzymatic DKR. Thus, further studies aimed at the synthesis of (-)-lyrinidine will be carried out in our research group. Key words: alkaloids, (+)-bernumidine, (-)-lirinidine, chemoenzymatic dynamic kinetic resolution, total synthesis.