A comparative study on the crystal structure of bicycle analogues to the natural phytotoxin helminthosporins

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dc.creatorBarbosa, Luiz Cláudio de Almeida
dc.creatorTeixeira, Róbson Ricardo
dc.creatorNogueira, Leonardo Brandão
dc.creatorMaltha, Celia Regina Alvares
dc.creatorDoriguetto, Antonio Carlos
dc.creatorMartins, Felipe Terra
dc.date.accessioned2023-12-14T13:28:01Z
dc.date.available2023-12-14T13:28:01Z
dc.date.issued2016
dc.description.abstractHerein we described structural insights of a series of analogues to helminthosporin phytotoxins. The key reaction used to prepare the compounds corresponded to the [3 + 4] cycloaddition between the oxyallyl cation generated from 2,4-dibromopentan-3-one and different furans. Their structures were confirmed upon IR, NMR and X-ray diffraction analyses. While bicycles 7, 8 and 9 crystallize in the centrosymmetric monoclinic space group P21/c, compound 10 was solved in the noncentrosymmetric orthorhombic space group P212121. The solid materials obtained were shown to be racemic crystals (7, 8, 9) or racemic conglomerate (10). In all compounds, there is formation of a bicycle featured by fused tetrahydropyranone and 2,5-dihydrofuran rings. They adopt chair and envelope conformations, respectively. Crystal packing of all compounds is stabilized through C–H•••O contacts. Conformational aspects as well as similarities and differences among the crystal structures of the synthesized analogues are discussed.
dc.identifier.citationBARBOSA, Luiz Cláudio de Almeida et al. A comparative study on the crystal structure of bicycle analogues to the natural phytotoxin helminthosporins. Journal of Molecular Structure, Amsterdam, v. 1105, p. 256-262, 2016. DOI: 10.1016/j.molstruc.2015.10.058. Disponível em: https://www.sciencedirect.com/science/article/abs/pii/S0022286015303604?via%3Dihub. Acesso em: 28 nov. 2023.
dc.identifier.doi10.1016/j.molstruc.2015.10.058
dc.identifier.issne- 1872-8014
dc.identifier.issn0022-2860
dc.identifier.urihttps://www.sciencedirect.com/science/article/abs/pii/S0022286015303604?via%3Dihub
dc.language.isoeng
dc.publisher.countryHolanda
dc.publisher.departmentInstituto de Química - IQ (RMG)
dc.rightsAcesso Restrito
dc.titleA comparative study on the crystal structure of bicycle analogues to the natural phytotoxin helminthosporins
dc.typeArtigo

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