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

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

Thomas D Avery  1 , Daniela Caiazza, Julie A Culbert, Dennis K Taylor, Edward R T Tiekink
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1,2-dioxines containing tethered hydroxyl functionality as convenient precursors for pyran syntheses

Thomas D Avery et al. J Org Chem. .

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.

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