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Molecules 2013, 18(1), 1174-1180; doi:10.3390/molecules18011174
Article

Diastereoselective Synthesis of 5-Hydroxy-8-methoxy-1-oxaspiro[5,5]undeca-7,10-diene-9-one

*  and
Department of Chemistry, University of Northern British Columbia, 3333 University Way, Prince George, BC V2N 4Z9, Canada
* Author to whom correspondence should be addressed.
Received: 13 December 2012 / Revised: 10 January 2013 / Accepted: 14 January 2013 / Published: 17 January 2013
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Abstract

A short five steps synthesis of the title compound from vanillin is described. The racemic spiroether 7 was obtained in 61% yield and in >99% diastereomeric excess (by 1H-NMR) from the corresponding phenolic derivative 3 by oxidation with lead (IV) acetate.
Keywords: synthesis; diastereoselective; spirolactone; spiroether; spirocompound; dienone; oxidation; lead tetraacetate synthesis; diastereoselective; spirolactone; spiroether; spirocompound; dienone; oxidation; lead tetraacetate
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Plourde, G.L.; Scully, T.W. Diastereoselective Synthesis of 5-Hydroxy-8-methoxy-1-oxaspiro[5,5]undeca-7,10-diene-9-one. Molecules 2013, 18, 1174-1180.

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