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Second-Generation, Biomimetic Total Synthesis of Chaetominine

  作者 COSTE ALEXIS; KARTHIKEYAN GANESAN; COUTY FRANCOIS; EVANO GWILHERM  
  选自 期刊  Synthesis;  卷期  2009年-17;  页码  2927-2934  
  关联知识点  
 

[摘要]A straightforward total synthesis of the potent anticancer agent (-)-chaetominine is reported. Central to this synthesis was a biomimetic oxidative cyclization of a tryptophanyl-alanine dipeptide, which provided a fully elaborated 1,2,3,4-tetrahydropyrido[2,3-b]indole. Reduction of this intermediate followed by spontaneous cyclization and installation of the side chain provided synthetic chactominine in a nine-step sequence in 14% overall yield starting from commercially available, inexpensive starting materials.

 
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