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An Access to Chiral beta-Benzyl-gamma-butyrolactones and Its Application to the Synthesis of Enantiopure (+)-Secoisolariciresinol, (-)-Secoisolariciresinol, and (-)-Enterolactone

  作者 ALLAIS FLORENT; PLA THOMAS J L; DUCROT PAULHENRI  
  选自 期刊  Synthesis;  卷期  2011年-9;  页码  1456-1464  
  关联知识点  
 

[摘要]Both enantiomers of secoisolariciresinol and enantiopure (-)-enterolactone were synthesized through a highly stereoselective convergent synthesis. An Evans diastereoselective alkylation followed by a substrate-induced diastereoselective alpha-alkylation of the newly formed optically active beta-benzyl-gamma-butyrolactone gave the beta-beta' linkage of the target skeleton. The (S,S)- and (R,R)-enantiomers of secoisolariciresinol and (-)-enterolactone were obtained in 12-14% (11 steps) and 20% (7 steps) overall yield, respectively.

 
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