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A Hetero-Diels−Alder Approach to Complex Pyrones:  An Improved Synthesis of the Spongistatin AB Spiroketal

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journal contribution
posted on 02.03.2006, 00:00 by Michael T. Crimmins, Aaron C. Smith
The conversion of a substituted dioxinone to a pyrone was used in an improved synthesis of the AB spiroketal subunit of the spongistatins. This transformation occurred via a hetero-Diels−Alder reaction of an acyl ketene with butyl vinyl ether. A double diastereoselective Mukaiyama aldol reaction is used to provide the hetero-Diels−Alder precursor.