title: Exploring skeletal diversity via ring contraction of glycal-derived scaffolds.
abstract: Aryl ether C-glycoside scaffolds have been prepared from tri-O-acetyl-D-glucal by C-glycosylation followed by allylic substitution with phenols mediated by Pd(0). The aryl ethers were subjected to either [3,3]-sigmatropic rearrangement to produce 3-pyranyl-phenols or Au(III)-mediated ring contraction to create highly substituted tetrahydrofurans. [structure: see text]
authors.affiliation: Department of Chemistry, Center for Chemical Methodology and Library Development at Boston University, Life Science and Engineering Building, Boston University, 24 Cummington Street, Boston, MA 02215, USA.
authors.forename: Adam R
authors.initials: AR
authors.lastname: Yeager
authors.forename: Geanna K
authors.initials: GK
authors.lastname: Min
authors.forename: John A
authors.initials: JA
authors.lastname: Porco
authors.forename: Scott E
authors.initials: SE
authors.lastname: Schaus
mesh_terms: D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry*; D006031:Glycosylation; D006046:Gold / Q000737:chemistry; D015394:Molecular Structure; D010636:Phenols / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D005663:Furans; D006027:Glycosides; D010636:Phenols; D006046:Gold