2,2-dimethyl cyclopentanones by acid catalyzed ring expansion of isopropenylcyclobutanols. A short synthesis of (+/-)-alpha-cuparenone and (+/-)-herbertene

Chem Commun (Camb). 2005 Aug 14:(30):3853-5. doi: 10.1039/b505707h. Epub 2005 Jun 23.

Abstract

2,2-dimethyl cyclopentanones are readily prepared by acid catalyzed ring expansion of isopropenylcyclobutanols; the method allows ready access to the family of sesquiterpenes cuparanes and herbertanes, as demonstrated by the synthesis of (+/-)-alpha-cuparenone and the direct precursor of (+/-)-herbertene.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acids / chemistry*
  • Catalysis
  • Cyclopentanes / chemical synthesis
  • Cyclopentanes / chemistry*
  • Methylation
  • Molecular Structure
  • Sesquiterpenes / chemical synthesis*
  • Sesquiterpenes / chemistry

Substances

  • Acids
  • Cyclopentanes
  • Sesquiterpenes
  • alpha-cuparenone
  • herbertene
  • cyclopentanone