Tandem Favorskii intermediate/cyclization leading to tricyclo[] decanediones Academic Article uri icon


MeSH Major

  • Pulmonary Disease, Chronic Obstructive
  • Smoking
  • Wnt Proteins
  • beta Catenin


  • The mechanism of dehydrobromination of the bromodiketone 8 leading to the unusual ring system of tricyclo[]decanediones (9 and 10) is described. An entry into the ring system of the sesquiterpenoid hydrocarbons copaene and ylangene, 8 to 9, is achieved in three steps starting with enone 6. Compound 9 was either derived from a direct internal SN2 cyclization of 8 or the Favorskii intermediate 8a. Formation of compound 10, on the other hand, can only occur via the Favorskii intermediate 8a. Structure assignments of 9 and 10 were determined using both one- and two-dimensional NMR experiments. Copyright © Taylor & Francis Group, LLC.

publication date

  • March 9, 2006



  • Academic Article


Digital Object Identifier (DOI)

  • 10.1080/00397910500466207

Additional Document Info

start page

  • 929

end page

  • 934


  • 36


  • 7