1,2-dioxines containing tethered hydroxyl functionality as convenient precursors for pyran syntheses

Thomas D Avery; Daniela Caiazza; Julie A Culbert; Dennis K Taylor; Edward R T Tiekink

doi:10.1021/jo050806n

1,2-dioxines containing tethered hydroxyl functionality as convenient precursors for pyran syntheses

J Org Chem. 2005 Oct 14;70(21):8344-51. doi: 10.1021/jo050806n.

Authors

Thomas D Avery¹, Daniela Caiazza, Julie A Culbert, Dennis K Taylor, Edward R T Tiekink

Affiliation

¹ Department of Chemistry, University of Adelaide, South Australia 5005, Australia.

PMID: 16209577
DOI: 10.1021/jo050806n

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Anticholesteremic Agents / chemistry
Antimitotic Agents / chemistry
Heterocyclic Compounds, 1-Ring / chemistry*
Hydroxyl Radical / chemistry*
Molecular Structure
Pyrans / chemical synthesis*
Pyrans / chemistry*

Substances

Anticholesteremic Agents
Antimitotic Agents
Heterocyclic Compounds, 1-Ring
Pyrans
Hydroxyl Radical