Síntese de novas fitotoxinas derivadas do 8- oxabiciclo[ 3. 2. 1] oct- 6- en- 3- ona

dc.creatorBarbosa, Luiz C. A.
dc.creatorMaltha, Célia R. A.
dc.creatorDemuner, Antônio J.
dc.creatorGanen, Flávia R.
dc.creatorSilva, Antônio A. da
dc.date2019-05-03T13:10:47Z
dc.date2019-05-03T13:10:47Z
dc.date2005-05
dc.date.accessioned2023-09-27T22:21:47Z
dc.date.available2023-09-27T22:21:47Z
dc.identifier1678-7064
dc.identifierhttp://dx.doi.org/10.1590/S0100-40422005000300015
dc.identifierhttp://www.locus.ufv.br/handle/123456789/24979
dc.identifier.urihttps://repositorioslatinoamericanos.uchile.cl/handle/2250/8974137
dc.descriptionThe [4+3] cycloaddition was utilized in order to prepare 8-oxabicyclo[3.2.1]oct-6-en-3-one (1) derivatives. The correspondent acetonide 6 was converted into several alcohols (11-16). Addition of aryllithium reagents to 6 resulted in 3-(2-fluorophenyl)-6,7-exo-isopropylidenedioxy -8-oxabicyclo[3.2.1]octan-3a-ol (11, 72%) and 3-(2,4-dimethoxyphenyl)-6,7-exo-isopropylidenedioxy-8-oxabicyclo[3.2.1]octan -3a-ol (16, 20%). The 3-butyl-6,7-exo-isopropylidenedioxy-8-oxabicyclo[3.2.1]octan-3 a-ol (15, 56%) was obtained through a Grignard reaction. Reduction of 6 resulted in 6,7-exo-isopropylidenedioxy-8-oxabicyclo[3.2.1]octan-3 b-ol (7, 62%) and 6,7-exo-isopropylidenedioxy-8-oxabicyclo[3.2.1]octan-3 a-ol (8, 20%). The alcohols were treated with thionyl chloride in pyridine, and the corresponding alkenes were obtained with 31-80% yield. The effect of these compounds on the development of radicle and aerial parts of Sorghum bicolor was evaluated.
dc.formatpdf
dc.formatapplication/pdf
dc.languagepor
dc.publisherQuímica Nova
dc.relationv. 28, n. 3, p. 444- 450, mai.- jun. 2005
dc.rightsOpen Access
dc.subject[ 4+ 3] cycloaddition
dc.subjectOxyallyl cations
dc.subjectHerbicides
dc.titleSíntese de novas fitotoxinas derivadas do 8- oxabiciclo[ 3. 2. 1] oct- 6- en- 3- ona
dc.typeArtigo


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