From galactose to highly functionalized seven- and eight-membered carbocyclic rings by ring-closing metathesis

Org Lett. 2000 Aug 24;2(17):2651-4. doi: 10.1021/ol006182j.

Abstract

[reaction: see text]A short synthesis of highly functionalized seven- and eight-membered carbocyclic rings from galactose derivatives has been achieved. The key steps are a zinc-mediated reductive ring opening of 6-iodogalactopyranoses and a subsequent ring-closing olefin metathesis using Grubbs' ruthenium catalyst.

MeSH terms

  • Catalysis
  • Crystallography, X-Ray
  • Cyclization
  • Galactose / chemistry*
  • Molecular Conformation
  • Ruthenium / chemistry
  • Thermodynamics
  • Zinc / chemistry

Substances

  • Ruthenium
  • Zinc
  • Galactose