Intramolecular iron-mediated diene/olefin cyclocoupling: formation of carbon spirocycles

Org Lett. 2004 Jul 22;6(15):2535-8. doi: 10.1021/ol040036m.

Abstract

[reaction: see text] A short and convenient diastereoselective synthesis of all-carbon spirocylic molecules was developed. A straightforward protocol that involves rearrangement of the diene-Fe(CO)(3) complex followed by cyclization delivers the desired product. The reaction substrates were easily prepared by reaction of an appropriate nucleophile and a cyclohexadienyl-Fe(CO)(3) cation.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Alkenes / chemistry*
  • Catalysis
  • Cyclization
  • Diterpenes / chemistry
  • Iron / chemistry*
  • Polycyclic Sesquiterpenes
  • Spiro Compounds / chemical synthesis*
  • Stereoisomerism
  • Terpenes / chemistry

Substances

  • Alkenes
  • Diterpenes
  • Polycyclic Sesquiterpenes
  • Spiro Compounds
  • Terpenes
  • elisabethin A
  • cedrol
  • Iron