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Org Lett. 2008 Mar 6;10(5):721-4. doi: 10.1021/ol7029068. Epub 2008 Feb 12.

An efficient synthesis of highly functionalized [5,6] aromatic spiroketals by hetero-Diels-Alder reaction.

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  • 1State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P.R. China.


A hetero-Diels-Alder reaction of vinyl sulfoxides with o-quinone methides precursor constructs highly functionalized [5,6] aromatic spiroketal skeletons in moderate to good yields with high regioselectivity. The two functional groups (ketone and olefin) can be further subjected to many synthetic transformations.

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