Exploring skeletal diversity via ring contraction of glycal-derived scaffolds.
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]
Yeager
Adam R
AR
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.
Min
Geanna K
GK
Porco
John A
JA
Schaus
Scott E
SE
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
D005663:Furans; D006027:Glycosides; D010636:Phenols; D006046:Gold