Total synthesis of (±)-perophoramidine
Total synthesis of (±)-perophoramidine
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DOI：
10.1021/ja049569g
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发表时间：
2004-04-28
影响因子：
15
通讯作者：
Funk, RL
中科院分区：
文献类型：
--
作者：
Fuchs, JR;Funk, RL
首次全合成了外消旋的perophoramidine。关键步骤的特征在于通过碱促进的3-烷基吲哚和3-溴-3-烷基吲哚啉-2-酮之间的碳碳键形成来高度立体选择性地引入邻位季中心。这种转化可能通过3-烷基吲哚与3-烷基吲哚-2-酮中间体的共轭加成或狄尔斯-桤木环加成进行。
The first total synthesis of racemic perophoramidine is described. The key step features the highly stereoselective introduction of the vicinial quaternary centers via base-promoted carbon−carbon bond formation between a 3-alkylindole and a 3-bromo-3-alkylindolin-2-one. This transformation presumably proceeds through a conjugate addition or Diels−Alder cycloaddition of the 3-alkylindole with a 3-alkylindol-2-one intermediate.