Total synthesis of serofendic acids A and B employing tin-free homoallyl-homoallyl radical rearrangement
Total synthesis of serofendic acids A and B employing tin-free homoallyl-homoallyl radical rearrangement
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DOI：
10.1021/ol051411t
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发表时间：
2005-09-01
期刊：
影响因子：
5.2
通讯作者：
Ihara, M
中科院分区：
文献类型：
--
作者：
Toyota, M;Asano, T;Ihara, M
本文报道了血清芬酸A（1a）和B（1B）的全合成。该方法的关键战略要素涉及新的无锡homoallyl-homoallyl自由基重排5的双环[2.2.2]辛烷环系统4的建设。此外，基于硫代甲醇钠的Michael反应，实现了阿西瑞烯酸甲酯2向血清芬酸A（1a）和B（1 B）的转化。
Total syntheses of serofendic acids A (1a) and B (1b) are described. The key strategic element of the approach involves the novel tin-free homoallyl-homoallyl radical rearrangement of 5 for the construction of bicyclo[2.2.2]octane ring system 4. In addition, the conversion of methyl atisirenoate 2 to serofendic acids A (1a) and B (1b) was achieved on the basis of the Michael reaction of sodium thiomethoxide.