A New, Asymmetric Synthesis of Lipids and Phospholipids

Journal of Organic Chemistry

Volumn 52, Issue 22, 1987, Pages 4973-4977

  Burgos, Carmen E ^a   Ayer, Donald E ^a   Johnson, Roy A ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCEROL 1 STEARATE; GLYCEROL DERIVATIVE; PHOSPHOLIPID; UNCLASSIFIED DRUG;

DRUG STRUCTURE; DRUG SYNTHESIS; METHODOLOGY; NONHUMAN; THEORETICAL STUDY;

EID: 0023608120     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00231a025     Document Type: Article

References (28)

1. For a personal account, see: Baer, E. J. Am. Oil Chem. Soc. 1965, 42. 257.
2. Fischer, H. O. L.; Baer, E. Naturwissenschaften 1937, 25, 589.
3. Baer, E.: Fischer, H. O. L. J. Biol. Chem. 1939, 128, 463.
4. Baer, E.; Kates, M. J. Am. Chem. Soc. 1950, 72, 942.
5. Lok, C. M.; Ward, J. P.; van Dorp, D. A. Chem. Phys. Lipids 1976, 16, 115.
6. Eibl, H. Chem. Phys. Lipids 1980, 26, 405.
7. Eibl, H. Liposomes: From Physical Structure to Therapeutic Applications; Knight, C. G., Ed.; Elsevier/North-Holland Biomedical Press: New York, 1981; Chapter 2.
8. Eibl, H. Angew. Chem., Int. Ed. Engl. 1984, 23, 257.
9. Slotboom, A. J.; Verheij, H. M.; de Haas, G. H. Chem. Phys. Lipids 1973,11, 295.
10. Eibl, H.; Kovatchev, S. Methods Enzymol., 1981, 72. 632.
11. Eibl, H.; Kovatchev, S. Methods Enzymol., 1981, 72. 632.
12. Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, 5976.
13. Klunder, J. M.; Ko, S. Y.; Sharpless, K. B. J. Org. Chem. 1986, 51, 3710.
14. Kleemann, A.; Wagner, R. Glycidol; Huthig: New York, 1981.
15. Hendrickson, H. S.; Hendrickson, E. K.; Dybvig, R. H. J. Lipid Res. 1983, 24, 1532.
16. Lok, C. M.; Mank, A. P. J.; Ward, J. P. Chem. Phys. Lipids 1985, 36, 329. dZlantanos S. N.; Sagredos, A. N.; Papageorgiou, V. P. J. Am. Oil Chem. Soc. 1985, 62, 1575.
17. Hansen, R. M.; Sharnless, K. B. J. Org. Chem. 1986. 51. 1922.
18. Caron, M.; Sharpless, K. B. J. Org. Chem. 1985, 50, 1557.
19. Bender, S. L. Ph.D. Thesis, Harvard University, 1986. We thank
20. Sowden, J. C.; Fischer, H. O. L. J. Am. Chem. Soc. 1942, 64, 1291.
21. Baer, E.; Fischer, H. O. L. J. Am. Chem. Soc. 1945, 67, 2031.
22. Hill, J. G.; Sharpless, K. B.; Exon, C. M.; Regenye, R. Org. Synth. 1984, 63, 66.
23. Hendrickson, H. S.; Hendrickson, E. K.; Rustad, T. J. J. Lipid Res. 1987, 28. 864.
24. Dale, J. A.; Dull, D.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543.
25. Dodd, G. H.; Golding, B. T.; Ivannou, P. V. J. Chem. Soc., Chem. Commun. 1975, 249.
26. Batten, R. J.; Dixon, A. J.; Taylor, R. J. K.; Newton, R. F. Synthesis 1980. 234.
27. Stepanov, A. E.; Shvets, V. I. Chem. Phys. Lipids 1986, 41, 1. Ramirez, F.; Marecek, J. F. Synthesis 1985, 449.
28. Eibl, H.; Nicksch, A. Chem. Phys. Lipids 1978, 22, 1.