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

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

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Received: 13 December 2012; in revised form: 10 January 2013 / Accepted: 14 January 2013 / Published: 17 January 2013
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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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