1,2-dioxines containing tethered hydroxyl functionality as convenient precursors for pyran syntheses.
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.
Avery
Thomas D
TD
Department of Chemistry, University of Adelaide, South Australia 5005, Australia.
Caiazza
Daniela
D
Culbert
Julie A
JA
Taylor
Dennis K
DK
Tiekink
Edward R T
ER
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*
D000924:Anticholesteremic Agents; D050256:Antimitotic Agents; D006573:Heterocyclic Compounds, 1-Ring; D011714:Pyrans; D017665:Hydroxyl Radical