Síntese e avaliação da atividade fitotóxica de novos análogos oxigenados do ácido helmintospórico
Autor(a) principal: | |
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Data de Publicação: | 2003 |
Outros Autores: | , , , |
Tipo de documento: | Artigo |
Idioma: | por |
Título da fonte: | LOCUS Repositório Institucional da UFV |
Texto Completo: | http://dx.doi.org/10.1590/S0100-40422003000500006 http://www.locus.ufv.br/handle/123456789/24965 |
Resumo: | 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. |
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Barbosa, Luiz Cláudio de AlmeidaDemuner, Antônio JacintoMaltha, Célia Regina ÁlvaresSilva, Patrícia Silvana daSilva, Antônio Alberto da2019-05-03T11:56:50Z2019-05-03T11:56:50Z2003-091678-7064http://dx.doi.org/10.1590/S0100-40422003000500006http://www.locus.ufv.br/handle/123456789/24965Several 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.porQuímica Novav. 26, n. 5, p. 655- 660, set.- out. 2003[ 3+ 4] cycloadditionHelminthosporic acidHerbicidesSíntese e avaliação da atividade fitotóxica de novos análogos oxigenados do ácido helmintospóricoinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfinfo:eu-repo/semantics/openAccessreponame:LOCUS Repositório Institucional da UFVinstname:Universidade Federal de Viçosa (UFV)instacron:UFVORIGINALartigo.pdfartigo.pdftexto completoapplication/pdf198063https://locus.ufv.br//bitstream/123456789/24965/1/artigo.pdf8f2f7c66f7a84ba4ea12c7683cadbcf2MD51LICENSElicense.txtlicense.txttext/plain; charset=utf-81748https://locus.ufv.br//bitstream/123456789/24965/2/license.txt8a4605be74aa9ea9d79846c1fba20a33MD52123456789/249652019-05-03 09:00:31.144oai:locus.ufv.br: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Repositório InstitucionalPUBhttps://www.locus.ufv.br/oai/requestfabiojreis@ufv.bropendoar:21452019-05-03T12:00:31LOCUS Repositório Institucional da UFV - Universidade Federal de Viçosa (UFV)false |
dc.title.pt-BR.fl_str_mv |
Síntese e avaliação da atividade fitotóxica de novos análogos oxigenados do ácido helmintospórico |
title |
Síntese e avaliação da atividade fitotóxica de novos análogos oxigenados do ácido helmintospórico |
spellingShingle |
Síntese e avaliação da atividade fitotóxica de novos análogos oxigenados do ácido helmintospórico Barbosa, Luiz Cláudio de Almeida [ 3+ 4] cycloaddition Helminthosporic acid Herbicides |
title_short |
Síntese e avaliação da atividade fitotóxica de novos análogos oxigenados do ácido helmintospórico |
title_full |
Síntese e avaliação da atividade fitotóxica de novos análogos oxigenados do ácido helmintospórico |
title_fullStr |
Síntese e avaliação da atividade fitotóxica de novos análogos oxigenados do ácido helmintospórico |
title_full_unstemmed |
Síntese e avaliação da atividade fitotóxica de novos análogos oxigenados do ácido helmintospórico |
title_sort |
Síntese e avaliação da atividade fitotóxica de novos análogos oxigenados do ácido helmintospórico |
author |
Barbosa, Luiz Cláudio de Almeida |
author_facet |
Barbosa, Luiz Cláudio de Almeida Demuner, Antônio Jacinto Maltha, Célia Regina Álvares Silva, Patrícia Silvana da Silva, Antônio Alberto da |
author_role |
author |
author2 |
Demuner, Antônio Jacinto Maltha, Célia Regina Álvares Silva, Patrícia Silvana da Silva, Antônio Alberto da |
author2_role |
author author author author |
dc.contributor.author.fl_str_mv |
Barbosa, Luiz Cláudio de Almeida Demuner, Antônio Jacinto Maltha, Célia Regina Álvares Silva, Patrícia Silvana da Silva, Antônio Alberto da |
dc.subject.pt-BR.fl_str_mv |
[ 3+ 4] cycloaddition Helminthosporic acid Herbicides |
topic |
[ 3+ 4] cycloaddition Helminthosporic acid Herbicides |
description |
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. |
publishDate |
2003 |
dc.date.issued.fl_str_mv |
2003-09 |
dc.date.accessioned.fl_str_mv |
2019-05-03T11:56:50Z |
dc.date.available.fl_str_mv |
2019-05-03T11:56:50Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://dx.doi.org/10.1590/S0100-40422003000500006 http://www.locus.ufv.br/handle/123456789/24965 |
dc.identifier.issn.none.fl_str_mv |
1678-7064 |
identifier_str_mv |
1678-7064 |
url |
http://dx.doi.org/10.1590/S0100-40422003000500006 http://www.locus.ufv.br/handle/123456789/24965 |
dc.language.iso.fl_str_mv |
por |
language |
por |
dc.relation.ispartofseries.pt-BR.fl_str_mv |
v. 26, n. 5, p. 655- 660, set.- out. 2003 |
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info:eu-repo/semantics/openAccess |
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openAccess |
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Química Nova |
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Química Nova |
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