From galactose to highly functionalized seven- and eight-membered carbocyclic rings by ring-closing metathesis.
[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.
Hanna
I
I
Laboratoire de Synthèse Organique associé au CNRS, Ecole Polytechnique, Palaiseau, France. hanna@poly.polytechnique.fr
Ricard
L
L
D002384:Catalysis; D018360:Crystallography, X-Ray; D003500:Cyclization; D005690:Galactose / Q000737:chemistry*; D008968:Molecular Conformation; D012428:Ruthenium / Q000737:chemistry; D013816:Thermodynamics; D015032:Zinc / Q000737:chemistry
D012428:Ruthenium; D015032:Zinc; D005690:Galactose