Síntese de novos herbicidas derivados do 1, 2a, 4a, 5- tetrametil- 8- oxabiciclo[ 3. 2. 1] oct- 6- en- 3- ona

• Autor(a) principal: Barbosa, Luiz Cláudio de Almeida
• Data de Publicação: 2004
• Outros Autores: Maltha, Célia Regina Álvares, Demuner, Antônio Jacinto, Filomeno, Claudinei Andrade, Silva, Antônio Alberto da
• Tipo de documento: Artigo
• Idioma: por
• Título da fonte: LOCUS Repositório Institucional da UFV
• Texto Completo: http://dx.doi.org/10.1590/S0100-40422004000200013; http://www.locus.ufv.br/handle/123456789/24980
• topic: [ 3+ 4] cycloaddition; Oxyallyl cations; Herbicides

In this paper we report the synthesis of biologically active compounds through a [3+4] cycloaddition reaction to produce the main frame structure, followed by several conventional transformations. The 1,2a,4a,5-tetramethyl-8-oxabicyclo[3.2.1]oct-6-en-3-one (11) obtained from a [3+4] cycloaddition reaction was converted into 1,2a,4a,5-tetramethyl-6,7-exo-isopropylidenedioxi-8 -oxabicyclo[3.2.1]octan-3-one (13) in 46% yield. This was further converted into the alcohols 1,2a,4a,5-tetramethyl-6,7-exo-isopropylidenedioxi-8-oxabicyclo[3.2.1]octan-3 a-ol (14), 1,2a,4a,5-tetramethyl-6,7-exo-isopropylidenedioxi-8 -oxabicyclo[3.2.1]octan-3b-ol (15), 1,2a,4a,5-tetramethyl-3-butyl-6,7-exo-isopropylidenedioxi-8-oxabicyclo[3.2.1]octan-3 a-ol (17), 1,2a,4a,5-tetramethyl-3-hexyl-6,7-exo-isopropylidenedioxi-8-oxabicyclo[3.2.1]octan-3 a-ol (18) and 1,2a,4a,5-tetramethyl-3-decyl-6,7-exo-isopropylidenedioxi-8-oxabicyclo[3.2.1]octan-3 a-ol (19). Dehydration of 17, 18 and 19 with thionyl chloride in pyridine resulted in the alkenes 20, 21 and 22 in ca. 82% - 89% yields from starting alcohols. The herbicidal activity of the compounds synthesized was evaluated at a concentration of 100 µg g-1. The most active compound was 21 causing 42,7% inhibition against Cucumis sativus L.