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Suzuki-Miyaura Coupling Based Enantioselective Synthesis of (+)-epi-Clausenamide and the Enantiomer of Its 3-Deoxy Analogue

  作者 ZHANG LU; ZHOU YUMEI; YU XIAOMING  
  选自 期刊  SYNLETT;  卷期  2012年-8;  页码  1217-1220  
  关联知识点  
 

[摘要]The first enantioselective synthesis of two biologically interesting close analogues of clausenamide, namely (+)-epi-clausenamide and (-)-3-deoxy-epi-clausenamide, was reported. Key steps of the synthesis included construction of the chiral pyrrolinone intermediates from D- and L-serine derivatives, introduction of the C4-phenyl by Suzuki-Miyaura coupling and establishment of the C6 configuration by a threo-selective Grignard reaction. Optimization of the key Suzuki-Miyaura coupling reaction was described in detail.

 
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