Synthesis of drynaran and analogues

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dc.creatorMendes, Lorena Lessa
dc.creatorVarejão, Jodieh Oliveira Santana
dc.creatorMartins, Felipe Terra
dc.creatorAraujo Neto, João Honorato de
dc.creatorVarejão, Eduardo Vinícius Vieira
dc.date.accessioned2023-11-06T14:56:00Z
dc.date.available2023-11-06T14:56:00Z
dc.date.issued2022
dc.description.abstractIn 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.
dc.identifier.citationMENDES, 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.
dc.identifier.doi10.1016/j.molstruc.2021.131673
dc.identifier.issne- 1872-8014
dc.identifier.issn0022-2860
dc.identifier.urihttps://www.sciencedirect.com/science/article/abs/pii/S0022286021018019?via%3Dihub
dc.language.isoeng
dc.publisher.countryHolanda
dc.publisher.departmentInstituto de Química - IQ (RMG)
dc.rightsAcesso Restrito
dc.subjectDrinaria bonii
dc.subjectHMF
dc.subjectCrossed aldol condensation
dc.subjectDiastereoselective reaction
dc.subjectX-ray diffraction analysis
dc.titleSynthesis of drynaran and analogues
dc.typeArtigo

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