Síntese e atividade fitotóxica de 2-fenil-6,7-exo-isopropilidenodioxi-8-oxabiciclo [3.2.1]oct-2-eno

Barbosa, Luiz C. A.; Demuner, Antônio J.; Costa, Adílson Vidal; Borges, Eduardo E.L.; Mann, John

doi:10.1590/s0100-40422000000400006

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“…Bioensaios realizados utilizando diversas espécies de culturas e de plantas daninhas como plantas indicadoras evidenciaram o potencial herbicida de derivados do 8-oxabiciclo[3.2.1]oct-6-en-3-ona (1) [5][6][7][8][9][10][11] , obtido pela reação de cicloadição [4+3] entre cátions oxialílicos e dienos (Figura 2) 12 .…”

Section: Introductionunclassified

“…Em um dos bioensaios realizados observou-se que a inibição de crescimento sobre o sistema radicular de Sorghum bicolor L. causada pelo composto 2, na concentração de 250 µg mL -1 , foi de 83% 6 . Para os compostos 3, 4 e 5, na concentração de 6,6 µg g -1 , também foi observada inibição sobre o crescimento radicular de S. bicolor (54,4, 59,4 e 66,3%, respectivamente) 10 .…”

Section: Introductionunclassified

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Síntese de novas fitotoxinas derivadas do 8-oxabiciclo[3.2.1]oct-6-en-3-ona

et al. 2005

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Recebido em 27/4/04; aceito em 22/9/04; publicado na web em 2/2/05 SYNTHESIS OF NEW PHYTOTOXINS DERIVED FROM 8-OXABICYCLO[3.2.1]OCT-6-EN-3-ONE. The [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-3α-ol (11, 72%) and 3-(2,4-dimethoxyphenyl)-6,7-exo-isopropylidenedioxy-8-oxabicyclo[3.2.1]octan-3α-ol (16, 20%). The 3-butyl-6,7-exo-isopropylidenedioxy-8-oxabicyclo[3.2.1]octan-3α-ol (15, 56%) was obtained through a Grignard reaction. Reduction of 6 resulted in 6,7-exo-isopropylidenedioxy-8-oxabicyclo[3.2.1]octan-3β-ol (7, 62%) and 6,7-exoisopropylidenedioxy-8-oxabicyclo[3.2.1]octan-3α-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.

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