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Syntheses of Prekinamycin and a Tetracyclic Quinone from Common Synthetic Intermediates

  作者 Kimura, S; Kobayashi, S; Kumamoto, T; Akagi, A; Sato, N; Ishikawa, T  
  选自 期刊  Helvetica Chimica Acta;  卷期  2011年94-4;  页码  578-591  
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[摘要]Towards total synthesis of a series of kinamycin and related antibiotics via common synthetic intermediates, total synthesis of prekinamycin was achieved via Suzuki coupling of naphthaleneboronic acid and bromobenzene derivative, intramolecular Friedel-Crafts reaction of 2-(naphthalen-2-yl) benzoic acid, and diazotization in ten steps from 3,5-dimethylphenol. Synthetic studies towards kinamycin antibiotics was also examined, and the tetracyclic quinone core for kinamycins was synthesized. Palladium-catalyzed site-selective hydroxylation of a benzoic acid derivative with the AB-D ring part was successfully applied to the selective D-ring functionalizations.

 
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