Use of fluoroalkyl as a latent group for internal alkylation: application to the synthesis of bridged tetrahydrofluorenones

Org Lett. 2008 Jul 17;10(14):2983-5. doi: 10.1021/ol800971f. Epub 2008 Jun 13.

Abstract

Tetrahydrofluorenones which possess a C9a-fluoroalkyl substituent were efficiently converted to tetrahydrofluorenones which contain a ring bridging C9a-C2. Conditions include a stepwise sequence of conversion to an alkyl bromide followed by treatment with base, and a direct cyclization by treatment with lithium chloride in DMF heated to 150 degrees C.

MeSH terms

  • Alkylation
  • Bridged-Ring Compounds / chemical synthesis
  • Catalysis
  • Cyclization
  • Estrogen Receptor beta / agonists
  • Fluorenes / chemical synthesis*
  • Hydrocarbons, Fluorinated / chemistry*
  • Molecular Structure

Substances

  • Bridged-Ring Compounds
  • Estrogen Receptor beta
  • Fluorenes
  • Hydrocarbons, Fluorinated