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Synthesis of Tubuphenylalanines via Ireland-Claisen Rearrangement

  作者 BECKER DOMINIC; KAZMAIER ULI  
  选自 期刊  Journal of Organic Chemistry;  卷期  2013年78-1;  页码  59-65  
  关联知识点  
 

[摘要]The Ireland-Claisen rearrangement is the central step in the synthesis of tubuphenylalanine, a key building block of the highly antitumor-active tubulysins. The rearrangement of substituted beta-amino acid ally! esters, in combination with subsequent decarboxylation and oxidative cleavage of the double bond, allows the highly stereoselective introduction of substituents into the alpha-position of the resulting gamma-amino acids.

 
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