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

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Avery, Thomas D.
Caiazza, Daniela
Culbert, Julie A.
Taylor, Dennis K.
Tiekink, Edward
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2005
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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 ?-hydroxy enones followed by intramolecular oxa-Michael addition of the tethered hydroxyl group.

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Journal of Organic Chemistry

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70

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Medicinal and Biomolecular Chemistry

Organic Chemistry

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