Indium-mediated stereoselective synthesis of truncated, 6- and 7-carbon sialic acids

Synlett

Volumn , Issue 12, 2002, Pages 2104-2106

  Warwel, Mathias ^a   Fessner, Wolf Dieter ^a  

^a DARMSTADT UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

Allylations; Barbier type reactions; Indium; Sialic acids; amino aldehydes

Indexed keywords

ACRYLIC ACID; ETHYL 2 (BROMOMETHYL) ACRYLATE; SIALIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; OZONOLYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0036456034     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-35564     Document Type: Article

References (46)

1. (a) Angata, T.; Varki, A. Chem. Rev. 2002, 102, 439.
2. (b) Roy, R.; Laferrière, C. A.; Pon, R. A. Methods Enzymol. 1994, 247, 351.
3. (c) Corfield, A. P.; Schauer, R. In Sialic Acids, Chemistry, Metabolism and Function; Schauer, R., Ed.; Springer Verlag: New York, 1982, 5.
4. (d) Vliegenthart, J. F. G., Mamerling, J. P. In Sialic Acids, Chemistry, Metabolism and Function; Schauer, R., Ed.; Springer Verlag: New York, 1982, 59.
5. (a) Vimr, E.; Lichtensteiger, C. Trends Microbiol. 2002, 10, 254.
6. (b) Kiefel, M. J.; von Itzstein, M. Chem. Rev. 2002, 102, 471.
7. (c) Jaeken, J.; Matthijs, G. Annu. Rev. Genomics Hum. Genet. 2001, 2, 129.
8. (d) Schauer, R. Glycoconjugate J. 2000, 17, 485.
9. (e) Crocker, P. R.; Varki, A. Trends Immunol. 2001, 22, 337.
10. (f) Sillanaukee, P.; Ponnio, M.; Jaaskelainen, I. P. Eur. J. Clin. Invest. 1999, 29, 413.
11. (g) Rosenberg, S. Biology of the Sialic Acids; Plenum Press: New York, 1995.
12. (a) For a review, see: Fessner, W.-D.; Walter, C. Top. Curr. Chem. 1996, 184, 97.
13. (b) Augé, C.; David, S.; Gautheron, C.; Veyrières, A. Tetrahedron Lett. 1985, 26, 2439.
14. (c) Simon, E. S.; Bednarski, M. D.; Whitesides, G. M. J. Am. Chem. Soc. 1988, 110, 7159.
15. (d) Schrell, A.; Whitesides, G. M. Liebigs Ann. Chem. 1990, 1111.
16. (e) Lin, C.-H.; Sugai, T.; Halcomb, R. L.; Ichikawa, Y.; Wong, C. H. J. Am. Chem. Soc. 1992, 114, 10138.
17. (f) Mahmoudian, M.; Noble, D.; Drake, C. S.; Middleton, R. F.; Montgomery, D. S.; Piercey, J. E.; Ramlakhan, D.; Todd, M.; Dawson, M. J. Enzyme Microb. Technol. 1997, 20, 393.
18. (a) For a review, see: Li, C.-J.; Chan, T.-H. Tetrahedron 1999, 55, 11149.
19. (b) Li, C.-J.; Chan, T.-H. J. Chem. Soc., Chem. Commun. 1992, 747.
20. (c) Kim, E.; Gordon, D. M.: Schmid, W.; Whitesides, G. M. J. Org. Chem. 1993, 58, 5500.
21. (d) Gordon, D. M.; Whitesides, G. M. J. Org. Chem. 1993, 58, 7937.
22. (e) Li, C. J.; Lee, M. C.; Wei, Z. Y.; Chan, T. H. Can. J. Chem. 1994, 72, 1181.
23. (f) Chan, T.-H.; Lee, M.-C. J. Org. Chem. 1995, 60, 4228.
24. (g) Choi, S.-K.; Lee, S.; Whitesides, G. M. J. Org. Chem. 1996, 61, 8739.
25. (h) Banwell, M. G.; Savi, C. D.; Watson, K. Chem. Commun. 1998, 1189.
26. (a) Suttajit, M.; Urban, C.; McLean, R. L. J. Biol. Chem. 1971, 246, 810.
27. (b) Kim, M.-J.; Hennen, W. J.; Sweers, H. M.; Wong, C.-H. J. Am. Chem. Soc. 1988, 110, 6481.
28. (c) Fitz, W.; Schwark, J. R.; Wong, C.-H. J. Org. Chem. 1995, 60, 3663.
29. (a) Kuhn, R.; Gauhe, A. Chem. Ber. 1965, 98, 395.
30. (b) McLean, R. L.; Suttajit, M.; Beidler, J.; Winzler, R. J. J. Biol. Chem. 1971, 246, 803.
31. (c) Peters, B. P.; Aronson, N. N. Carbohydr. Res. 1976, 47, 345.
32. (d) Reuter, G.; Schauer, R.; Szeiki, C.; Kamerling, J. P.; Vliegenthart, J. F. G. Glycoconjugate J. 1989, 6, 35.
33. Synthesis of derivatives of 10a: (a) from D-glucuronolactone: Vlahov, I. R.; Vlahova, P. I.; Schmidt, R. R. Tetrahedron Lett. 1991, 32, 7025. (b) From D-serine: Chappell, M. D.; Halcomb, R. L. Org. Lett. 2000, 2, 2003. (c) From L-ascorbic acid: Banwell, M.; De Savi, C.; Hockless, D.; Watson, K. Chem. Commun. 1998, 645.
34. Synthesis of derivatives of 10a: (a) from D-glucuronolactone: Vlahov, I. R.; Vlahova, P. I.; Schmidt, R. R. Tetrahedron Lett. 1991, 32, 7025. (b) From D-serine: Chappell, M. D.; Halcomb, R. L. Org. Lett. 2000, 2, 2003. (c) From L-ascorbic acid: Banwell, M.; De Savi, C.; Hockless, D.; Watson, K. Chem. Commun. 1998, 645.
35. Synthesis of derivatives of 10a: (a) from D-glucuronolactone: Vlahov, I. R.; Vlahova, P. I.; Schmidt, R. R. Tetrahedron Lett. 1991, 32, 7025. (b) From D-serine: Chappell, M. D.; Halcomb, R. L. Org. Lett. 2000, 2, 2003. (c) From L-ascorbic acid: Banwell, M.; De Savi, C.; Hockless, D.; Watson, K. Chem. Commun. 1998, 645.
36. Knorst, M.; Fessner, W.-D. Adv. Synth. Catal. 2001, 343, 698.
37. (a) Jurczak, J.; Golebiowski, A. Chem. Rev. 1989, 89, 149.
38. (b) Reetz, M. T. Angew. Chem., Int. Ed. Engl. 1991, 30, 1531.
39. (c) Steurer, S.; Podlech, J. Eur. J. Org. Chem. 1999, 1551.
40. Hung, R. R.; Straub, J. A.; Whitesides, G. M. J. Org. Chem. 1991, 56, 3849.
41. Waldmann, H.; Sebastian, D. Chem. Rev. 1994, 94, 911.
42. +, 95)
43. Warwel, M.; Fessner, W.-D. Synlett 2000, 6, 865.
44. The origin of the pronounced selectivity at low pH has not been thoroughly investigated yet but it may be speculated that protonation of the electrophile will lead to a tighter transition state for the addition. For an in-depth discussion, see: Paquette, L. A.; Mitzel, T. M. J. Am. Chem. Soc. 1996, 118, 1931.
45. Lemieux, G. A.; Bertozzi, C. R. Chem. Biol. 2001, 8, 265.
46. Villieras, J.; Rambaud, M. Org. Synth. 1988, 66, 220.