Synthesis and phytogrowth properties of oxabicyclic analogues related to helminthosporin.
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.
Barbosa
Luiz Cláudio Almeida
LC
Department of Chemistry, Federal University of Viçosa, 36570-000, Viçosa, Minas Gerais, Brazil. lcab@ufv.br
Nogueira
Leonardo Brandão
LB
Maltha
Célia Regina Alvares
CR
Teixeira
Róbson Ricardo
RR
Silva
Antônio Alberto
AA
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
D001952:Bridged-Ring Compounds; D006540:Herbicides; D012717:Sesquiterpenes; C534562:helminthosporic acid; C083652:helminthosporol; C015256:helminthosporal