Synthesis of sialic acids via desymmetrization by ring-closing metathesis

Journal of Organic Chemistry

Volumn 67, Issue 24, 2002, Pages 8489-8499

  Voight, Eric A ^a   Rein, Christian ^a   Burke, Steven D ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

METATHESIS;

ANTIGENS; DERIVATIVES; SYNTHESIS (CHEMICAL);

ORGANIC ACIDS;

N ACETYLNEURAMINIC ACID; NITROGEN; ONCOFETAL ANTIGEN; OXYGEN; SIALIC ACID DERIVATIVE; ONCOFETAL ANTIGENS; TUMOR ANTIGEN;

ARTICLE; DEAMINATION; RING CLOSING METATHESIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE; ORGANIC CHEMISTRY; STEREOISOMERISM; THIN LAYER CHROMATOGRAPHY;

ANTIGENS, NEOPLASM; CATALYSIS; CHEMISTRY, ORGANIC; CHROMATOGRAPHY, THIN LAYER; CYCLIZATION; MOLECULAR STRUCTURE; N-ACETYLNEURAMINIC ACID; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; SIALIC ACIDS; STEREOISOMERISM;

EID: 0037195673     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0263014     Document Type: Article

References (74)

1. (a) Kiefel, M. J.; von Itzstein, M. Chem. Rev. 2002, 102, 471-490.
2. (b) von Itzstein, M.; Thompson, R. J. Top. Curr. Chem. 1997, 186, 119-170.
3. (a) Schauer, R.; Kelm, S.; Reuter, G.; Roggentin, P.; Shaw, L. Biochemistry and role of sialic acids. In Biology of the Sialic Acids; Rosenberg, A., Ed.; Plenum: New York, 1995; p 7.
4. (b) Schauer, R. Adv. Carbohydr. Chem. Biochem. 1982, 40, 131.
5. (c) Reutter, W.; Köttgen, E.; Bauer, C.; Gerok, W. Biological significance of sialic acids. In Sialic Acids - Chemistry, Metabolism and Function: Schauer, R., Ed.; Springer, Berlin Heidelberg, New York, 1982; p 263.
6. (a) Nadano, D.; Iwasaki, M.; Endo, S.; Kitajima, K.; Inoue, S.; Inoue, Y. J. Biol. Chem. 1986, 261, 11550-11557.
7. (b) Inoue, S.; Lin, S.-L.; Chang, T.; Wu, S.-H.; Yao, C.-W.; Chu, T.-Y.; Troy, F. A., II; Inoue, Y. J. Biol. Chem. 1998, 273, 27199-27204.
8. For reviews, see ref 1 and: (a) DeNinno, M. P. Synthesis 1991, 583-593. (b) Tuppy, H.; Gottschalk, A. The Structure of sialic acids and their quantitation. In Glycoproteins. Their Composition, Structure and Function; Gottschalk, A., Ed.; Elsevier: Amsterdam, The Netherlands, 1972; p 403.
9. For reviews, see ref 1 and: (a) DeNinno, M. P. Synthesis 1991, 583-593. (b) Tuppy, H.; Gottschalk, A. The Structure of sialic acids and their quantitation. In Glycoproteins. Their Composition, Structure and Function; Gottschalk, A., Ed.; Elsevier: Amsterdam, The Netherlands, 1972; p 403.
10. For recent chemical syntheses of Neu5Ac, see: (a) Liu, K.-G.; Yan, S.; Wu, Y.-L.; Yao, Z.-J. J. Org. Chem. 2002, 67, 6758. (b) Li, L.-S.; Wu, Y.-L.; Wu, Y. Org. Lett. 2000, 2, 891-894. (c) Banwell, M.; Savi, C. D.; Watson, K. J. Chem. Soc., Perkin Trans. 1 1998, 2251-2252. (d) Takahashi, T.; Tsukamoto, H.; Kurosaki, M.; Yamada, H. Synlett 1997, 1065-1066.
11. For recent chemical syntheses of Neu5Ac, see: (a) Liu, K.-G.; Yan, S.; Wu, Y.-L.; Yao, Z.-J. J. Org. Chem. 2002, 67, 6758. (b) Li, L.-S.; Wu, Y.-L.; Wu, Y. Org. Lett. 2000, 2, 891-894. (c) Banwell, M.; Savi, C. D.; Watson, K. J. Chem. Soc., Perkin Trans. 1 1998, 2251-2252. (d) Takahashi, T.; Tsukamoto, H.; Kurosaki, M.; Yamada, H. Synlett 1997, 1065-1066.
12. For recent chemical syntheses of Neu5Ac, see: (a) Liu, K.-G.; Yan, S.; Wu, Y.-L.; Yao, Z.-J. J. Org. Chem. 2002, 67, 6758. (b) Li, L.-S.; Wu, Y.-L.; Wu, Y. Org. Lett. 2000, 2, 891-894. (c) Banwell, M.; Savi, C. D.; Watson, K. J. Chem. Soc., Perkin Trans. 1 1998, 2251-2252. (d) Takahashi, T.; Tsukamoto, H.; Kurosaki, M.; Yamada, H. Synlett 1997, 1065-1066.
13. For recent chemical syntheses of Neu5Ac, see: (a) Liu, K.-G.; Yan, S.; Wu, Y.-L.; Yao, Z.-J. J. Org. Chem. 2002, 67, 6758. (b) Li, L.-S.; Wu, Y.-L.; Wu, Y. Org. Lett. 2000, 2, 891-894. (c) Banwell, M.; Savi, C. D.; Watson, K. J. Chem. Soc., Perkin Trans. 1 1998, 2251-2252. (d) Takahashi, T.; Tsukamoto, H.; Kurosaki, M.; Yamada, H. Synlett 1997, 1065-1066.
14. For recent chemical syntheses of KDN, see: (a) Warwel, M.; Fessner, W. D. Synlett 2000, 6, 865-867. (b) Banwell, M.; De Savi, C.; Watson, K. J. Chem. Soc., Chem. Commun. 1998, 1189-1190. (c) Tsukamoto, H.; Takahashi, T. Tetrahedron Lett. 1997, 38, 6415-6418. (d) Salagnad, C.; Gödde, A.; Ernst, B.; Kragl, U. Biotechnol. Prog. 1997, 13, 810-813.
15. For recent chemical syntheses of KDN, see: (a) Warwel, M.; Fessner, W. D. Synlett 2000, 6, 865-867. (b) Banwell, M.; De Savi, C.; Watson, K. J. Chem. Soc., Chem. Commun. 1998, 1189-1190. (c) Tsukamoto, H.; Takahashi, T. Tetrahedron Lett. 1997, 38, 6415-6418. (d) Salagnad, C.; Gödde, A.; Ernst, B.; Kragl, U. Biotechnol. Prog. 1997, 13, 810-813.
16. For recent chemical syntheses of KDN, see: (a) Warwel, M.; Fessner, W. D. Synlett 2000, 6, 865-867. (b) Banwell, M.; De Savi, C.; Watson, K. J. Chem. Soc., Chem. Commun. 1998, 1189-1190. (c) Tsukamoto, H.; Takahashi, T. Tetrahedron Lett. 1997, 38, 6415-6418. (d) Salagnad, C.; Gödde, A.; Ernst, B.; Kragl, U. Biotechnol. Prog. 1997, 13, 810-813.
17. For recent chemical syntheses of KDN, see: (a) Warwel, M.; Fessner, W. D. Synlett 2000, 6, 865-867. (b) Banwell, M.; De Savi, C.; Watson, K. J. Chem. Soc., Chem. Commun. 1998, 1189-1190. (c) Tsukamoto, H.; Takahashi, T. Tetrahedron Lett. 1997, 38, 6415-6418. (d) Salagnad, C.; Gödde, A.; Ernst, B.; Kragl, U. Biotechnol. Prog. 1997, 13, 810-813.
18. (a) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012-3043.
19. (b) Schrock, R. R. Tetrahedron 1999, 55, 8141-8153.
20. (c) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450.
21. (d) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-388.
22. (e) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036-2056.
23. Burke, S. D.; Müller, N.; Beaudry, C. M. Org. Lett. 1999, 1, 1827-1829.
24. Burke, S. D.; Voight, E. A. Org. Lett. 2001, 3, 237-240.
25. Voight, E. A.; Rein, C; Burke, S. D. Tetrahedron Lett. 2001, 42, 8747-8749.
26. (a) Poss, C. S.; Schreiber, S. L. Acc. Chem. Res. 1994, 27, 9-17.
27. (b) Magnuson, S. R. Tetrahedron 1995, 51, 2167-2213.
28. Burke, S. D.; Sametz, G. M. Org. Lett. 1999, 1, 71-74.
29. Dondoni, A.; Marra, A.; Merino, P. J. Am. Chem. Soc. 1994, 116, 3324-3336.
30. Brown, H. C.; Jadhav, P. K.; Bhat, K. S. J. Am. Chem. Soc. 1988, 110, 1535-1538.
31. Takano, S.; Iwabuchi, Y.; Ogasawara, K. J. Am. Chem. Soc. 1991, 113, 2786-2787.
32. Mattson, A.; Orrenius, C.; Öhrner, N.; Unelius, R.; Hult, K.; Norin, T. Acta Chem. Scand. 1996, 50, 918-921.
33. Kang, S. H.; Ryu, D. H. J. Chem. Soc., Chem. Commun. 1996, 355-356.
34. Yates, P.; Schwartz, D. A. Can. J. Chem. 1983, 61, 509-518.
35. Grandberg, I. I.; Zuyanova, T. I. Khim. Geterotsikl. Soedin. 1968, 4, 875-877.
36. (a) Danishefsky, S. J.; DeNinno, M. P.; Chen, S. J. Am. Chem. Soc. 1988, 110, 3929-3940.
37. (b) Danishefsky, S. J.; DeNinno, M. P. J. Org. Chem. 1986, 51, 2615-2617.
38. Katritzky, A. R.; Lang, H.; Wang, Z.; Zhang, Z.; Song, H. J. Org. Chem. 1995, 60, 7619-7624.
39. (a) Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483-2547.
40. (b) Becker, H.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 448-451.
41. (a) Yamada, T.; Kakinuma, K.; Oshima, T. Chem. Lett. 1987, 1745-1748.
42. (b) Azam, S.; D'Souza, A. A.; Wyatt, P. B. J. Chem. Soc., Perkin Trans. 1 1996, 621-627.
43. (c) Arvanitis, E.; Motevalli, M.; Wyatt, P. B. Tetrahedron Lett. 1996, 37, 4277-4280.
44. (d) Sloan, M. J.; Kirk, K. L. Tetrahedron Lett. 1997, 38, 1677-1680.
45. (e) Eguchi, T.; Morita, M.; Kakinuma, K. J. Am. Chem. Soc. 1998, 120, 5427-5433.
46. Kossmehl, G.; Frohberg, H.-C. Chem. Ber. 1986, 119, 50-64.
47. N2 displacement product.
48. Martinelli, M. J.; Nayyar, N. K.; Moher, E. D.; Dhokte, U. P.; Pawlak, J. M.; Vaidyanathan, R. Org. Lett. 1999, 1, 447-450.
49. (a) David, S.; Hanessian, S. Tetrahedron 1985, 41, 643-663.
50. (b) Grindley, T. B. Adv. Carbohydr. Chem. Biochem. 1998, 53, 16-142.
51. The tin-catalyzed monobenzoylation of various vicinal diols has been recently reported: (a) Maki, T.; Iwasaki, F.; Matsumura, Y. Tetrahedron Lett. 1998, 39, 5601-5604. (b) Iwasaki, F.; Maki, T.; Onomura, O.; Nakashima, W.; Matsumura, Y. J. Org. Chem. 2000, 65, 996-1002.
52. The tin-catalyzed monobenzoylation of various vicinal diols has been recently reported: (a) Maki, T.; Iwasaki, F.; Matsumura, Y. Tetrahedron Lett. 1998, 39, 5601-5604. (b) Iwasaki, F.; Maki, T.; Onomura, O.; Nakashima, W.; Matsumura, Y. J. Org. Chem. 2000, 65, 996-1002.
53. (a) Huffman, J. W.; Desai, R. C. Synth. Commun. 1983, 13, 553-557.
54. (b) Torisawa, Y.; Okabe, H.; Ikegami, S. Chem. Lett. 1984, 1555-1556.
55. (c) Sato, K.; Yoshitomo, A. Chem. Lett. 1995, 39-40.
56. (d) Shimizu, T.; Hiranuma, S.; Nakata, T. Tetrahedron Lett. 1996, 37, 6145-6148.
57. (e) Pour, M.; Willis, A. C.; Furber, M.; Mander, L. N. Tetrahedron 1998, 54, 13833-13850.
58. Carlsen, P. H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936-3938.
59. (a) Mononen, I.; Lengstad, B.; Lönngren, J. Acta Chem. Scand. B 1980, 34, 775-776.
60. (b) Nakamura, M.; Takayanagi, H.; Furuhata, K.; Ogura, H. Chem. Pharm. Bull. 1992, 40, 879-885.
61. (a) For a recent example, see: Schmidt, B. J. Chem. Soc., Perkin Trans. 1 1999, 2627-2637.
62. (b) For a review, see: Parker, R. E.; Isaacs, N. S. Chem. Rev. 1959, 59, 737.
63. (a) Paulsen, H.; Heitmann, A. C. Liebigs Ann. Chem. 1988, 11, 1061-1071.
64. (b) Zbiral, E.; Schmid, W. Monatsh. Chem. 1985, 116, 253-262.
65. Takatori, K.; Kajiwara, M. Synlett 1995, 3, 280-282.
66. Surprisingly, attempted epoxidation using Mitsunobu conditions gave almost exclusively the undesired β-epoxide despite close precedent suggesting that 10 should be the major product. Thomson, R.; von Itzstein, M. Carbohydr. Res. 1995, 274, 29-44.
67. Monneret, C.; Risse, S.; Ardouin, P.; Gouyette, A. Eur. J. Med. Chem. Chim. Ther. 2000, 35, 137-146.
68. (a) Baker, R.; Boyes, R. H. O.; Broom, D. M. P.; O'Mahony, M. J.; Swain, C. J. J. Chem. Soc., Perkin Trans. 1 1987, 1613-1621.
69. (b) Kãlé, V. N.; Clive, D. L. J. J. Org. Chem. 1984, 49, 1554-1563.
70. (a) Julina, R.; Müller, I.; Vasella, A.; Wyler, R. Carbohydr. Res. 1987, 164, 415-432.
71. (b) Okamoto, K.; Kondo, T.; Goto, T. Bull. Chem. Soc. Jpn. 1987, 60, 631-636.
72. (c) Ogura, H.; Furuhata, K. Carbohydr. Res. 1986, 158, 37-51.
73. (d) Zbiral, E.; Brandstetter, H. H. Monatsh. Chem. 1985, 116, 87-98.
74. (e) Ponpipom, M. M.; Bugianesi, R. L.; Shen, T. Y. Can. J. Chem. 1980, 58, 214-220.