Total Synthesis of 4-Azaeudistomin Y1 and Analogues by Inverse-ElectronDemand Diels–Alder Reactions of 3-Aminoindoles with 1,3,5-Triazines
Total Synthesis of 4-Azaeudistomin Y1 and Analogues by Inverse-ElectronDemand Diels–Alder Reactions of 3-Aminoindoles with 1,3,5-Triazines
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DOI：
10.1055/s-0032-1316857
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发表时间：
2013-02
期刊：
影响因子：
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通讯作者：
Guoxing Xu;Lianyou Zheng;Q. Dang;X. Bai
中科院分区：
文献类型：
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作者：
Guoxing Xu;Lianyou Zheng;Q. Dang;X. Bai
以3-氨基吲哚为亲二烯体，通过反电子需求Diels-Alder（IDA）反应，高效、高产率地合成了4-氮杂-β-咔啉.因为N1-未保护的3-氨基吲哚显示差的热稳定性，所以开发了将叔丁氧基羰基保护基的去除与IDA反应组合的一锅法方案。该方法以1H-吲哚-3-基氨基甲酸叔丁酯为原料，以优异的产率得到了相应的IDA产物.采用IDA新方法合成了4-氮卓异雄酮Y 1，经4步反应，总收率为57%。此外，该化学适合于通过Friedel-Crafts酰化反应或酰胺形成反应快速制备可用于探索C1-位置处的结构-活性关系的类似物。
A new inverse-electron-demand Diels–Alder (IDA) reaction of 3-aminoindoles as dienophiles was developed for the efficient preparation of 4-aza-β-carbolines in high yields. Because N 1 -unprotected 3-aminoindoles show poor thermal stability, a one-pot protocol was developed that combines the removal of tert -butoxycarbonyl protecting groups with the IDA reaction. This protocol, using tert -butyl 1 H -indol-3-ylcarbamates as reactants, gave the corresponding IDA products in excellent yields. The new IDA methodology was used in a total synthesis of 4-azaeudistomin Y 1 , which was obtained in 57% overall yield in four steps. Moreover, the chemistry is suitable for the rapid preparation, through either Friedel–Crafts acylation or amide-formation reactions, of analogues that are useful for exploring structure–activity relationships at the C 1 -position.