A selective intramolecular 5-exo-dig or 6-endo-dig cyclization en route to 2-furanone or 2-pyrone containing tricyclic scaffolds

J Org Chem. 2011 Dec 2;76(23):9817-25. doi: 10.1021/jo201952p. Epub 2011 Oct 31.

Abstract

Ringfused bicyclic 2-pyridones exhibit interesting biological properties against pili assembly in uropathogenic Escherichia coli (Pinkner, J. S. et al. Proc. Natl. Acad. Sci. U. S. A.2006, 103, 17897-17902; Åberg, V. et al. Org. Biomol. Chem.2007, 5, 1827-1834) as well as curli formation (Cegelski, L. et al. Nat. Chem. Biol.2009, 5, 913-919). In the search for new ring-fused central fragments, highly selective synthetic routes to the 2-furanone or 2-pyrone containing tricyclic scaffolds 1 and 2 have been developed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclization
  • Furans / chemical synthesis*
  • Furans / chemistry
  • Molecular Structure
  • Pyrones / chemical synthesis*
  • Pyrones / chemistry

Substances

  • Furans
  • Pyrones