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Rapid access to synthetic lysobisphosphatidic acids using P(III) chemistry
J Chevallier1, N Sakai, F Robert
1Department of Organic Chemistry, University of Geneva, CH-1211 Geneva, Switzerland.
Organic Letters
|July 13, 2000
Abstract:
An expeditious route to synthetic lysobisphosphatidic acid S,S-1, its enantiomer, and regioisomers is reported. Synthetic difficulties concerning lipid stability and stereochemistry are bypassed using a phosphite triester approach in combination with multiple silyl protection. Spectroscopic studies evidence that acyl group migration in S,S-1 is accelerated by nonpolar solvents and inhibited by pyridine.