Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5271755 | Tetrahedron Letters | 2013 | 31 Pages |
Abstract
Highly oxygenated cyclohexanes (known as cyclitols or carba-sugars) were synthesized regiospecifically and stereoselectively via a key inverse electron demand Diels-Alder cycloaddition of electron poor 2-pyrones with electron rich tert-butyldimethylsilyl vinyl ether. The resulting [2.2.2]oxabicyclic lactones proved to be versatile synthons; syn-dihydroxylations were achieved with very high stereocontrol, with up to five stereocenters being produced from commercially available or easily prepared planar starting materials.
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Authors
Rachel D. Slack, Maxime A. Siegler, Gary H. Posner,