Synthesis of new phytotoxins derived from 8-oxabicyclo[3.2.1]oct-6-en-3-one

Quimica nova

Demuner, Antônio J.¹  Maltha, Célia R. A.¹  Silva, Antônio A. da¹  Barbosa, Luiz C. A.¹  Ganen, Flávia R.¹ 

[1] Universidade Federal de Viçosa, Viçosa

关键词: [;    4+3];    cycloaddition;    oxyallyl cations;    herbicides.;   

DOI  :  10.1590/S0100-40422005000300015

学科分类：化学（综合）

来源: Sociedade Brasileira de Quimica

【 摘 要 】

The [4+3] cycloadditionwas utilized in order to prepare 8-oxabicyclo[3.2.1]oct-6-en-3-one (1)derivatives. The correspondent acetonide 6 was converted into severalalcohols (11-16). Addition of aryllithium reagents to 6resulted 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-3a-ol (15, 56%) was obtained through a Grignardreaction. Reduction of 6 resulted in 6,7-exo-isopropylidenedioxy-8-oxabicyclo[3.2.1]octan-3b-ol (7, 62%) and 6,7-exo-isopropylidenedioxy-8-oxabicyclo[3.2.1]octan-3a-ol (8, 20%). The alcohols were treated withthionyl chloride in pyridine, and the corresponding alkenes were obtained with31-80% yield. The effect of these compounds on the development of radicle andaerial parts of Sorghum bicolor was evaluated.

【 授权许可】

CC BY