Síntese e avaliação da atividade fitotóxica de novos análogos oxigenados do ácido helmintospórico
dc.contributor.author | Barbosa, Luiz Cláudio de Almeida | |
dc.contributor.author | Demuner, Antônio Jacinto | |
dc.contributor.author | Maltha, Célia Regina Álvares | |
dc.contributor.author | Silva, Patrícia Silvana da | |
dc.contributor.author | Silva, Antônio Alberto da | |
dc.date.accessioned | 2019-05-03T11:56:50Z | |
dc.date.available | 2019-05-03T11:56:50Z | |
dc.date.issued | 2003-09 | |
dc.description.abstract | Several compounds related to helminthosporic acid (3) were synthesized via the [3+4] cycloaddition. The reaction of 3-hydroxymethyl-2-methylfuran (12) with 1,1,3,3-tetrabromo-4-methylpentan-2-one (13) resulted in 7-hydroxymethyl-4a-isopropyl-1a-methyl-8-oxabicyclo[3.2.1]oct-6-en-3-one (8) (37%) and 7-hydroxymethyl-2a-isopropyl-1a-methyl-8-oxabicyclo[3.2.1]oct-6-en-3-one (14) (12%), which were converted into 7-formyl-4a-isopropyl-1a-methyl-8-oxabicyclo[3.2.1]oct-6-en-3-one (16) (32% from 8) and 7-formyl-2a-isopropyl-1a-methyl-8-oxabicyclo[3.2.1]oct-6-en-3-one (18) (40% from 14), respectively. Reduction of (8) resulted in 7-hydroxymethyl-4a-isopropyl-1a-methyl-8-oxabicyclo[3.2.1]oct-6 -en-3a-ol (11) (63% from 8) and 7-hydroxymethyl-4a-isopropyl-1a-methyl-8-oxabicyclo[3.2.1]oct-6-en-3 b-ol (15) (30% from 8). The 4a-isopropyl-1a-methyl-3-oxo-8-oxabicyclo[3.2.1]oct-6-en-7-oic acid (19) was obtained by oxidation of (16) (78%). The results of biological tests are described in details. The best result was observed for compound (15) that caused 76% inhibition on the root growth of D. tortuosum. | en |
dc.format | pt-BR | |
dc.identifier.issn | 1678-7064 | |
dc.identifier.uri | http://dx.doi.org/10.1590/S0100-40422003000500006 | |
dc.identifier.uri | http://www.locus.ufv.br/handle/123456789/24965 | |
dc.language.iso | por | pt-BR |
dc.publisher | Química Nova | pt-BR |
dc.relation.ispartofseries | v. 26, n. 5, p. 655- 660, set.- out. 2003 | pt-BR |
dc.rights | Open Access | pt-BR |
dc.subject | [ 3+ 4] cycloaddition | pt-BR |
dc.subject | Helminthosporic acid | pt-BR |
dc.subject | Herbicides | pt-BR |
dc.title | Síntese e avaliação da atividade fitotóxica de novos análogos oxigenados do ácido helmintospórico | pt-BR |
dc.type | Artigo | pt-BR |