Synthesis of a novel cyclic pentacovalent phosphoenol ether derived from a dienone. Approaches to the syntheses of phosphonate analogs of sphingomyelin, sphingosine 1-phosphate and ceramide 1-phosphate

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.