Construction of the Zaragozic Acids Core Bicycle

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Abstract
Concise synthesis of the bicyclic core of zaragozic acids has been accomplished by the utilization of (2S,3S)-furylglycerol 7. The key features are based on the diastereoselective dihydroxylation of enone 8 followed by reduction of ketone 11 to control the stereochemistries at the C4-C6 positions of the target molecule. Addition of lithium trimethylsilylacetylide to aldehyde 20 provided propargyl alcohol 21, which was further transformed into the bicyclic core 25, a potent intermediate for the synthesis of zaragozic acids.

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