A selective intramolecular 5-exo-dig or 6-endo-dig cyclization en route to 2-furanone or 2-pyrone containing tricyclic scaffolds.
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.
Department of Chemistry, Umeå University, SE-90187 Umeå, Sweden.
Christoffer
C
Bengtsson
Fredrik
F
Almqvist
D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry
D005663:Furans; D011753:Pyrones