Total synthesis of alternariol
Total synthesis of alternariol
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DOI：
10.1021/jo050075r
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发表时间：
2005-04-15
影响因子：
3.6
通讯作者：
Metzler, M
中科院分区：
文献类型：
--
作者：
Koch, K;Podlech, J;Metzler, M
以苔黑酚和3，5-二甲氧基溴苯为起始原料，经七步反应合成了链格孢属真菌的有毒次级代谢产物链格孢醇。最长的线性序列由六个步骤组成。关键的反应是钯催化的Suzuki型偶联的orcinol衍生的硼酸与溴代间苯二酚醛。最后的脱甲基化以73%的产率提供含有较少部分的交链孢酚9-甲基醚（类似于20%）的交链孢酚。
Total synthesis of alternariol, a toxic secondary metabolite of various Alternaria fungi, was achieved in seven steps starting with orcinol and 3,5-dimethoxybromobenzene. The longest linear sequence consists of six steps. Key reaction is a palladium-catalyzed Suzuki-type coupling of an orcinol-derived boronic acid with a brominated resorcylic aldehyde. The final demethylation furnished alternariol in 73% yield containing a smaller fraction of alternariol 9-methyl ether (similar to 20%).