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A Bismuth(III)-Catalyzed Friedel-Crafts Cyclization and Stereocontrolled Organocatalytic Approach to (-)-Platensimycin

  作者 EEY STANLEY T C; LEAR MARTIN J  
  选自 期刊  Organic Letters;  卷期  2010年12-23;  页码  5510-5513  
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[摘要]A high yielding route to the (-)-platensimycin core is communicated. This entailed the discovery of Bi(OTf)(3) to catalyze a Friedel-Crafts cyclization of a free lactol, supplemented by LiClO4 to suppress the Lewis basicity of the sulfonate group. After TBAF-promotecl cyclodearomatization, a diastereoselective conjugate reduction of a dienone was achieved by adopting amine-based organocatalytic rationales to reverse the inherent steric control of the substrate.

 
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