ol0618252_si_001.pdf (2.73 MB)

Exploring Skeletal Diversity via Ring Contraction of Glycal-Derived Scaffolds

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journal contribution
posted on 26.10.2006, 00:00 by Adam R. Yeager, Geanna K. Min, John A. Porco,, Scott E. Schaus
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.