title: Diversity-oriented synthesis of a library of substituted tetrahydropyrones using oxidative carbon-hydrogen bond activation and click chemistry.
abstract: Eighteen (2RS,6RS)-2-(4-methoxyphenyl)-6-(substituted ethyl)dihydro-2H-pyran-4(3H)ones were synthesized via a DDQ-mediated oxidative carbon-hydrogen bond activation reaction. Fourteen of these tetrahydropyrans were substituted with triazoles readily assembled via azide-alkyne click-chemistry reactions. Examples of a linked benzotriazole and pyrazole motif were also prepared. To complement the structural diversity, the alcohol substrates were obtained from stereoselective reductions of the tetrahydropyrone. This library provides rapid access to structurally diverse non-natural compounds to be screened against a variety of biological targets.
authors.affiliation: Department of Chemistry and Center for Chemical Methodologies & Library Development, University of Pittsburgh, Pittsburgh, PA 15260, USA.
authors.forename: Nilesh
authors.initials: N
authors.lastname: Zaware
authors.forename: Matthew G
authors.initials: MG
authors.lastname: Laporte
authors.forename: Ramy
authors.initials: R
authors.lastname: Farid
authors.forename: Lei
authors.initials: L
authors.lastname: Liu
authors.forename: Peter
authors.initials: P
authors.lastname: Wipf
authors.forename: Paul E
authors.initials: PE
authors.lastname: Floreancig
mesh_terms: D057930:Click Chemistry / Q000379:methods*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011714:Pyrans / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D011714:Pyrans