An expeditious route to synthetic lysobisphosphatidic acid S,S-1, its enant
iomer, and regioisomers is reported. Synthetic difficulties concerning lipi
d stability and stereochemistry are bypassed using a phosphite triester app
roach in combination with multiple silyl protection. Spectroscopic studies
evidence that acyl group migration in S,S-1 is accelerated by nonpolar solv
ents and inhibited by pyridine.