title: 1,2-dioxines containing tethered hydroxyl functionality as convenient precursors for pyran syntheses.
abstract: 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 gamma-hydroxy enones followed by intramolecular oxa-Michael addition of the tethered hydroxyl group.
authors.affiliation: Department of Chemistry, University of Adelaide, South Australia 5005, Australia.
authors.forename: Thomas D
authors.initials: TD
authors.lastname: Avery
authors.forename: Daniela
authors.initials: D
authors.lastname: Caiazza
authors.forename: Julie A
authors.initials: JA
authors.lastname: Culbert
authors.forename: Dennis K
authors.initials: DK
authors.lastname: Taylor
authors.forename: Edward R T
authors.initials: ER
authors.lastname: Tiekink
mesh_terms: D000924:Anticholesteremic Agents / Q000737:chemistry; D050256:Antimitotic Agents / Q000737:chemistry; D006573:Heterocyclic Compounds, 1-Ring / Q000737:chemistry*; D017665:Hydroxyl Radical / Q000737:chemistry*; D015394:Molecular Structure; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D000924:Anticholesteremic Agents; D050256:Antimitotic Agents; D006573:Heterocyclic Compounds, 1-Ring; D011714:Pyrans; D017665:Hydroxyl Radical