A novel methodology for the synthesis of fumarates and maleates

Synlett

Volumn , Issue 12, 2006, Pages 1933-1937

  Price, Wayne S ^a   Fletcher, Steven ^a   Jorgensen, Michael R ^a,b   Miller, Andrew D ^a,b  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

^b IC Vec Ltd   (United Kingdom)

Author keywords

cis aconitic; Horner Wadsworth Emmons (HWE); Ozonolysis; PEGylated lipids; Wittig

Indexed keywords

ACONITIC ACID; ALPHA KETO ESTER DERIVATIVE; CHOLESTEROL; ESTER DERIVATIVE; FUMARIC ACID DERIVATIVE; LIPID; LIPOSOME; MALEIC ACID DERIVATIVE; PRODRUG; UNCLASSIFIED DRUG;

ARTICLE; DRUG DELIVERY SYSTEM; GENE DELIVERY SYSTEM; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HORNER WADSWORTH EMMONS REACTION; PH MEASUREMENT; STEREOCHEMISTRY; SYNTHESIS; WITTIG REACTION;

EID: 33747059316     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-948166     Document Type: Article

References (35)

1. (a) Kosterelos, K.; Miller, A. D. Chem. Soc. Rev. 2005, 970.
2. (b) Fenske, D. B.; Cullis, P. R. Methods Enzymol. 2005, 7.
3. Gabizon, A.; Papahadjopoulos, D. Proc. Natl. Acad. Sci. U.S.A. 1998, 6949.
4. Woodle, M. C.; Matthey, K. K.; Newman, M. S.; Hidayat, J. E.; Collins, L. R.; Redemann, C.; Martin, F. J.; Papahadjopolous, D. Biochim. Biophys. Acta 1992, 1105, 193.
5. (a) Holland, J. W.; Hui, C.; Cullis, P. R.; Madden, T. D. Biochemistry 1996, 35, 2618.
6. (b) Keller, M.; Harbottle, R. P.; Perouzel, E.; Colin, M.; Shah, L.; Rahim, A.; Vaysse, L.; Bergau, A.; Moritz, S.; Brahimi-Horn, C.; Coutelle, C.; Miller, A. D. ChemBioChem 2003, 4, 286.
7. Guo, X.; Szoka, F. C. Jr. Acc. Chem. Res. 2003, 36, 335.
8. Kirpotin, D.; Hong, K.; Mullah, N.; Papahadjopoulos, D.; Zalipsky, S. FEBS Lett. 1996, 388, 115.
9. Pak, C. C.; Ali, S.; Janoff, A. S.; Meers, P. Biochim. Biophys. Acta 1998, 1372, 13.
10. Kratz, F.; Beyer, U.; Schutte, M. T. Crit. Rev. Ther. Drug Carrier Sys. 1999, 245.
11. Zelphati, O.; Szoka, F. C. Proc. Natl. Acad. Sci. U.S.A. 1996, 95, 11493.
12. Askon, A.; Cho, M. J. J. Pharm. Sci. 2002, 91, 903.
13. (a) Guo, X.; Mackay, J. A.; Szoka, F. C. Biophys. J. 2003, 84, 1784.
14. (b) Guo, X.; Szoka, F. C. Bioconj. Chem. 2001, 12, 291.
15. (a) Hamann, P. R.; Hinman, L. M.; Hollander, I.; Beyer, C. F.; Lindh, D.; Holcomb, R.; Hallet, W.; Tsou, H. R.; Upeslacis, J.; Shochat, D.; Mountain, A.; Flowers, D. A.; Bernstein, I. Bioconjugate Chem. 2002, 13, 47.
16. (b) Ulbrich, K.; Etrych, T.; Chytil, P.; Pechar, M.; Jelinkova, M.; Rihova, B. Int. J. Pharm. 2004, 277, 63.
17. (c) Ulbrich, K.; Etrych, T.; Chytil, P.; Jelinkova, M.; Rihova, B. J. Controlled Release 2003, 87, 33.
18. (a) Shin, J.; Shum, P.; Thompson, D. H. J. Controlled Release 2003, 91, 187.
19. (b) Boomer, J. A.; Inerowicz, H. D.; Zhang, Z. Y.; Berstrand, N.; Edwards, K.; Kim, J. M.; Thompson, D. H. Langmuir 2003, 19, 6408.
20. (a) Alshamkhani, A.; Duncan, R. Int. J. Pharm. 1995, 122, 107.
21. (b) Reddy, J. A.; Low, P. S. J. Controlled Release 2000, 64, 2737.
22. (c) Drummond, D. C.; Daleke, D. L. Chem. Phys. Lipids 1995, 75, 27.
23. Bender, M. L. J. Am. Chem. Soc. 1957, 79, 1528.
24. (a) Ulbrich, K.; Etrych, T.; Chytil, P.; Jelinkova, M.; Rihova, B. J. Controlled Release 2003, 33.
25. (b) Yoo, H. S.; Lee, E. A.; Park, T. G. J. Controlled Release 2002, 17.
26. (c) Drummond, D. C.; Daleke, D. L. Chem. Phys. Lipids 1995, 27.
27. Fletcher, S.; Jorgensen, M. R.; Miller, A. D. Org Lett. 2004, 4245.
28. Shen, W. C.; Ryser, H. J. P. Biochem. Biophys. Res. Commun. 1981, 102, 1048.
29. Remenyi, J.; Balazs, B.; Toth, S.; Falus, A.; Toth, G.; Hudecz, F. Biochem. Biophys. Res. Commun. 2003, 303, 556.
30. Wasserman, H. H.; Ho, W.-B. J. Org. Chem. 1994, 4364.
31. 2 and stirred at -78 °C for 2 h until the solution turned colorless. The crude product was purified using flash chromatography on silica gel to afford the α-keto ester as a clear oil.
32. 2].
33. + + H], 333 (65), 316 (35), 277 (100) and 216 (33).
34. Diaz, M.; Branchadell, V.; Oliva, A.; Ortuno, R. M. Tetrahedron 1995, 51, 11841.
35. Gibson, F. S.; Bergmeier, S. C.; Rapoport, H. J. Org. Chem. 1994, 59, 3216.