Rapid access to synthetic lysobisphosphatidic acids using P-III chemistry

Authors
Chevallier, J Sakai, N Robert, F Kobayashi, T Gruenberg, J Matile, S
Citation
J. Chevallier et al., Rapid access to synthetic lysobisphosphatidic acids using P-III chemistry, ORG LETT, 2(13), 2000, pp. 1859-1861
Citations number
37
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
13
Year of publication
2000
Pages
1859 - 1861
Database
ISI
SICI code
1523-7060(20000629)2:13<1859:RATSLA>2.0.ZU;2-#
Abstract
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.