A Fully Palladium-Mediated Construction of Phenanthrenes and Naphthoxindoles

作者:Nassar Hardy Luma; Deraedt Christophe; Fouquet Eric; Felpin Francois Xavier*
来源:European Journal of Organic Chemistry, 2011, 2011(24): 4616-4622.
DOI:10.1002/ejoc.201100477

摘要

A fully palladium-catalyzed synthesis of unusual naphthoxindole alkaloids through a key intramolecular direct C-H arylation step leading to the formation of the phenanthrene core is described. The three-step process involves a highly efficient Heck coupling of aryl diazonium salts with phenyl-acrylates, giving the corresponding cis-stilbenes. Cyclization of stilbenes into phenanthrenes through a direct intramolecular C-H arylation, followed by a palladium-mediated cyclization of an amino ester, led to the formation of novel naphthoxindoles.

  • 出版日期2011-8