Multicomponent coupling approach to (±)-Frondosin B and a ring-expanded analogue
Multicomponent coupling approach to (±)-Frondosin B and a ring-expanded analogue
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DOI：
10.1021/ol035822q
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发表时间：
2004-02-19
期刊：
影响因子：
5.2
通讯作者：
Flynn, BL
中科院分区：
文献类型：
--
作者：
Kerr, DJ;Willis, AC;Flynn, BL
最近发现的多组分偶联反应可用于直接获得叶毛多辛 B 合成中的后期中间体。通过持续加热反应混合物，该中间体也可以有效地转化为叶毛多辛 B 的扩环类似物。提出了前所未有的串联 1,7-氢转移、8pi-电环化来解释这种扩环物质的形成。
A recently discovered multicomponent coupling reaction is used to give direct access to a late intermediate in the synthesis of frondosin B. This intermediate can also be efficiently converted to a ring-expanded analogue of frondosin B by sustained heating of the reaction mixture. An unprecedented tandem 1,7-hydrogen shift, 8pi-electrocyclization is proposed to explain the formation of this ring-expanded species.