title: Synthesis and phytogrowth properties of oxabicyclic analogues related to helminthosporin.
abstract: This investigation describes the synthesis and biological evaluation of a series of oxabicyclic analogues related to the helminthosporins. Four oxabicycles were prepared by [4+3] cycloaddition of an oxyallyl carbocation, generated in situ from 2,4-dibromopentan-3-one, with selected furans. Functional group manipulations of the oxabicyclic architecture generated nine further derivatives. The phytotoxic properties of these oxabicycles were evaluated as their ability to interfere with the growth of Sorghum bicolor and Cucumis sativus seedlings. In both species, the most active compounds were oxabicycles possessing a carbonyl group conjugated with a double bond.
authors.affiliation: Department of Chemistry, Federal University of Viçosa, 36570-000, Viçosa, Minas Gerais, Brazil. lcab@ufv.br
authors.forename: Luiz Cláudio Almeida
authors.initials: LC
authors.lastname: Barbosa
authors.forename: Leonardo Brandão
authors.initials: LB
authors.lastname: Nogueira
authors.forename: Célia Regina Alvares
authors.initials: CR
authors.lastname: Maltha
authors.forename: Róbson Ricardo
authors.initials: RR
authors.lastname: Teixeira
authors.forename: Antônio Alberto
authors.initials: AA
authors.lastname: Silva
mesh_terms: D001952:Bridged-Ring Compounds / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D018553:Cucumis sativus / Q000187:drug effects / Q000254:growth & development; D006540:Herbicides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D012717:Sesquiterpenes / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D045868:Sorghum / Q000187:drug effects / Q000254:growth & development; D013329:Structure-Activity Relationship
chemical_list: D001952:Bridged-Ring Compounds; D006540:Herbicides; D012717:Sesquiterpenes; C534562:helminthosporic acid; C083652:helminthosporol; C015256:helminthosporal