Abstract
The synthesis of a new pentacovalent oxaphospholene from a dienone, and its use as an enolate equivalent in the approach toward the syntheses of a phosphonate analog of sphingomyelin, sphingosine 1-phosphate and ceramide 1-phosphate is described. Condensation of the new P(V) reagent with an azodicarboxylate, followed by reduction of the ketone produced cis- and/or trans-oxazolidinones, potential precursors to the sphingomyelin, sphingosine and ceramide molecules. A study of reducing agents to produce the desired cis-oxazolidinone is presented.
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