1,2-dioxines containing tethered hydroxyl functionality as convenient precursors for pyran synthesis
Author(s)
Avery, Thomas D.
Caiazza, Daniela
Culbert, Julie A.
Taylor, Dennis K.
Tiekink, Edward
Griffith University Author(s)
Year published
2005
Metadata
Show full item recordAbstract
A new method for the construction of tetrahydropyrans derived from readily available 1,2-dioxines containing a tethered hydroxyl moiety is described. The reaction proceeds via a base-catalyzed rearrangement of the 1,2-dioxines to either the isomeric cis or trans ?-hydroxy enones followed by intramolecular oxa-Michael addition of the tethered hydroxyl group.A new method for the construction of tetrahydropyrans derived from readily available 1,2-dioxines containing a tethered hydroxyl moiety is described. The reaction proceeds via a base-catalyzed rearrangement of the 1,2-dioxines to either the isomeric cis or trans ?-hydroxy enones followed by intramolecular oxa-Michael addition of the tethered hydroxyl group.
View less >
View less >
Journal Title
Journal of Organic Chemistry
Volume
70
Publisher URI
Subject
Medicinal and Biomolecular Chemistry
Organic Chemistry