Structures, biological activities, and total syntheses of 13-hydroxy- and 13-acetoxy-14-nordehydrocacalohastine, novel modified furanoeremophilane-type sesquiterpenes from Trichilia cuneata
Structures, biological activities, and total syntheses of 13-hydroxy- and 13-acetoxy-14-nordehydrocacalohastine, novel modified furanoeremophilane-type sesquiterpenes from Trichilia cuneata
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DOI：
10.1021/ol050346k
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发表时间：
2005-04-28
期刊：
影响因子：
5.2
通讯作者：
Morimoto, Y
中科院分区：
文献类型：
--
作者：
Doe, M;Shibue, T;Morimoto, Y
13-Hydroxy-14-nordehydrocacalohastine（2）和13-acetoxy-14-nordehydrocacalohastine（3）是两个从Trichilia cuneata中分离得到的新的修饰的furanoeremophilane型倍半萜烯化合物，具有抑制线粒体和微粒体膜脂过氧化作用。通过钯催化的三组分偶联反应，在2-碘甲苯（7），1-戊烯-4-炔-3-醇（8）和乙氧亚甲基丙二酸二乙酯（9）之间实现了新化合物2和3的首次高度收敛的全合成。
13-Hydroxy-14-nordehydrocacalohastine (2) and 13-acetoxy-14-nordehydrocacalohastine (3), two novel modified furanoeremophilane-type sesquiterpenes isolated from Trichilia cuneata, showed inhibitory activities for membrane lipid peroxidation in mitochondria and microsomes. The first, highly convergent total syntheses of new compounds 2 and 3 have also been achieved via a palladium-mediated three-component coupling reaction between 2-iodotoluene (7), 1-penten-4-yn-3-ol (8), and diethyl ethoxymethylenemalonate (9).