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A NEW ENTRY TO THE SYNTHESIS OF PRIMIN VIA A B-ALKYL SUZUKI-MIYAURA CROSS-COUPLING REACTION

  作者 WATANABE KAZUHIRO; SUGIZAKI TOMOHIRO; TOZAWA YUMI; KATOH TADASHI  
  选自 期刊  Heterocycles;  卷期  2012年86-2;  页码  985-989  
  关联知识点  
 

[摘要]Primin, a biologically active benzoquinone natural product, was efficiently synthesized in 56% overall yield in six steps starting from commercially available 5-iodovanillin. The synthetic method involves crucial steps, including a B-alkyl Suzuki-Miyaura cross-coupling reaction to directly install an alkyl side chain in an aromatic ring and elaboration of quinone functionality by degradative oxidation using Fremy's salt to yield the target primin.

 
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