Development of the diastereoselective ETIC reaction: Application toward the total synthesis of Leucascandrolide A

ORGN 432

John R. Seiders II and Paul E. Floreancig. Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260
Efforts in our labs have demonstrated the ability to efficiently synthesize 2-substituted pyranones using enol acetates as carbon nucleophiles in electron transfer initiated cyclization (ETIC) reactions. The scope of these reactions has recently been expanded to provide a diastereoselective synthesis of 2,6-syn-disubstituted pyranones. We are currently exploring the reactivity of more complex substrates to test the limitations of this reaction for use in the total synthesis of Leucascandrolide A.

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