Fused tetracycles with a benzene or cyclohexadiene core: [2 + 2 + 2] cycloadditions on macrocyclic systems

Chem Commun (Camb). 2008 Sep 28:(36):4339-41. doi: 10.1039/b806524a. Epub 2008 Jul 16.

Abstract

A series of fused tetracycles with a benzene or cyclohexadiene core (2a-h) is satisfactorily prepared by intramolecular [2 + 2 + 2] cycloadditions of triynic and enediynic macrocycles (1a-h) under RhCl(PPh3)3 catalysis; the enantioselective cycloaddition of macrocycles 1b and 1e and gives chiral tetracycles with moderate enantiomeric excess.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemical synthesis*
  • Alkynes / chemistry
  • Benzene / chemistry*
  • Catalysis
  • Cyclization
  • Cyclohexenes / chemistry*
  • Heterocyclic Compounds, 4 or More Rings / chemical synthesis*
  • Heterocyclic Compounds, 4 or More Rings / chemistry
  • Macrocyclic Compounds / chemical synthesis
  • Macrocyclic Compounds / chemistry*
  • Molecular Structure
  • Organometallic Compounds / chemistry
  • Rhodium / chemistry
  • Stereoisomerism

Substances

  • Alkynes
  • Cyclohexenes
  • Heterocyclic Compounds, 4 or More Rings
  • Macrocyclic Compounds
  • Organometallic Compounds
  • Rhodium
  • Benzene