Exploration of the interrupted Fischer indolization reaction.

Exploration of the interrupted Fischer indolization reaction.
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DOI:
10.1016/j.tet.2010.02.050
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发表时间:
2010-06-26
期刊:
影响因子:
2.1
通讯作者:
Garg NK
Garg NK
中科院分区:
化学3区
文献类型:
--
作者:
Schammel AW;Boal BW;Zu L;Mesganaw T;Garg NK

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A convergent method to access the fused indoline ring system present in a multitude of bioactive molecules has been developed. The strategy involves the condensation of hydrazines with latent aldehydes to ultimately deliver indoline-containing products by way of an interrupted Fischer indolization sequence. The method is convergent, mild, operationally simple, broad in scope, and can be used to access enantioenriched products. In addition, our approach is amenable to the synthesis of furoindoline and pyrrolidinoindoline natural products as demonstrated by the concise formal total syntheses of physovenine and debromoflustramine B. The strategy will likely enable the synthesis of more complex targets such as the communesin alkaloids.
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