Synthesis of drynaran and analogues
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2022
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In a previous work, the natural compound drynaran, namely E-3-(5-hydroxymethyl)furan-2-yl)-2-phenylacrylaldehyde, was isolated from the Asian medicinal plant Drynaria bonii. Although this plant is used for several therapeutic purposes, drynaran was isolated in small quantities and, therefore, evaluated only for a few biological activities. Here, we propose a simple, fast, diastereoselective, and green synthesis of drynaran, using ethanol as solvent and 5-hydroxymethylfurfural as starting material. Drynaran was obtained in 66% yield and 98:2 E:Z diastereoisomeric ratio. The method was also used to produce a series of drynaran analogues, some of them as pure E-isomer and others in E:Z ratio of at least 90:10. Besides, five drynaran analogues formed crystals with suitable qualities for single-crystal X-ray diffraction data collection, and their crystal structures are described for the first time.
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Drinaria bonii, HMF, Crossed aldol condensation, Diastereoselective reaction, X-ray diffraction analysis
Citação
MENDES, Lorena Lessa et al. Synthesis of drynaran and analogues. Journal of Molecular Structure, Amsterdam, v. 1250, e131673, 2021. DOI: 10.1016/j.molstruc.2021.131673. Disponível em: https://www.sciencedirect.com/science/article/abs/pii/S0022286021018019?via%3Dihub. Acesso em: 31 out. 2023.