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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

✍ Scribed by Cynthia K McClure; Pranab K Mishra


Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
180 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis


The synthesis of a new pentacovalent oxaphospholene from a dienone, and its use as an enolate equivalent in the approach toward the syntheses of phosphonate analogs of sphingomyelin, sphingosine 1-phosphate and ceramide 1-phosphate are described. Condensation of the new P(V) reagent with an azodicarboxylate, followed by reduction of the ketone produced cisand/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.