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

doi:10.3390/molecules18011174

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

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

Guy L. Plourde* and Thomas W. Scully

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; in revised form: 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

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MDPI and ACS Style

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.

AMA Style

Plourde GL, Scully TW. Diastereoselective Synthesis of 5-Hydroxy-8-methoxy-1-oxaspiro[5,5]undeca-7,10-diene-9-one. Molecules. 2013; 18(1):1174-1180.

Chicago/Turabian Style

Plourde, Guy L.; Scully, Thomas W. 2013. "Diastereoselective Synthesis of 5-Hydroxy-8-methoxy-1-oxaspiro[5,5]undeca-7,10-diene-9-one." Molecules 18, no. 1: 1174-1180.

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