De novo sythesis of a D-galacturonic acid thioglycoside as key to the total synthesis of a glycosphingolipid from

Organic Letters

Volumn 10, Issue 8, 2008, Pages 1573-1576

  Yanoikuyae, Sphingomonas ^a   Stallforth, Pierre ^a   Adibekian, Alexander ^a   Seeberger, Peter H ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOSPHINGOLIPID; THIOGLYCOSIDE;

ARTICLE; CHEMISTRY; SPHINGOMONAS; SYNTHESIS;

GLYCOSPHINGOLIPIDS; SPHINGOMONAS; THIOGLYCOSIDES;

EID: 44449153699     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol800227b     Document Type: Article

References (59)

1. Willats, W. G. T.; McCartney, L.; Mackie, W.; Knox, J. P. Plant Mol. Biol. 2001, 47, 9.
2. (a) Katzenellenbogen, E.; Kocharova, N. A.; Zatonsky, G. V.; Korzeniowska-Kowal, A.; Shashkov, A. S.; Knirel, Y. A. Carbohydr. Res. 2003, 338, 2153.
3. (b) Rozalski, A.; Sidorczyk, Z.; Kotelko, K. Microbiol. Mol. Biol. Rev. 1997, 61, 65.
4. (a) Hakomori, S. I. Anna. Rev. Biochem. 1981, 50, 733.
5. (b) Wu, D.; Fujio, M.; Wong, C. H. Bioorg. Med. Chem. 2008, 16, 1073.
6. (a) Kinjo, Y.; Wu, D.; Kim, G.; Xing, G.-W.; Poles, M. A.; Ho, D. D.; Tsuji, M.; Kawahara, K.; Wong, C.-H.; Kronenberg, M. Nature 2005, 434, 520.
7. (b) Wu, D.; Xing, G. W.; Poles, M. A.; Horowitz, A.; Kinjo, Y.; Sullivan, B.; Bodmer-Narkevitch, V.; Plettenburg, O.; Kronenberg, M.; Tsuji, M.; Ho, D. D.; Wong, C. H. Proc. Natl. Acad. Set U.S.A. 2005, 102, 1351.
8. Kronenberg, M. Annu. Rev. Immunol. 2005, 23, 877.
9. (a) Paulsen, H. Angew. Chem., Int. Ed. Engl. 1982, 21, 155.
10. (b) Danishefsky, S. J.; McClure, K. F.; Randolph, J. T.; Ruggeri, R. B. Science 1993, 260, 1307.
11. (c) Sears, P.; Wong, C. H. Science 2001, 291, 2344.
12. (d) Plante, O. J.; Palmacci, E. R.; Seeberger, P. H. Science 2001, 291, 1523.
13. (e) Davis, B. G. J. Chem. Soc. Perkin Trans. 1 2000, 2137.
14. (f) Werz, D. B.; Ranzinger, R.; Herget, S.; Adibekian, A.; von der Lieth, C.-W.; Seeberger, P. H. ACS Chem. Biol. 2007, 2, 685.
15. (g) Varki, A. Glycobiology 1993, 3, 97.
16. (h) Roy, R. Drug Discovery Today, 2004, 1, 327.
17. (i) Dube, D. H.; Bertozzi, C. R. Nat. Rev. Drug Discovery 2005, 4, All.
18. (j) Garegg, P. J. Adv. Carbohydr. Chem. Biochem. 2004, 59, 69.
19. (k) Dwek, R. A. Chem. Rev. 1996, 96, 683.
20. (l) Babu, R. S.; Zhou, M.; O'Doherty, G. A. J. Am. Chem. Soc. 2004, 126, 3428.
21. (m) Zhou, M.; O'Doherty, G. A. Org. Lett. 2006, 8, 4339.
22. (n) van den Bos, L. J.; Codée, J. D. C; Litjens, R. E. J. N.; Dinkelaar, J.; Overkleeft, H. S.; van der Marel, G. A. Eur. J. Biochem. 2007, 3963.
23. For recent organocatalytic de novo syntheses of partially protected monosaccharides, see:
24. (a) Northrup, A. B.; MacMillan, D. W. C. Science 2004, 305, 1752.
25. (b) Enders, D.; Grondal, C. Angew. Chem. 2005, 117, 1235; Angew. Chem., Int. Ed. 2005, 44, 1210.
26. (c) Utsumi, N.; Imai, M.; Tanaka, F.; Ramasastry, S. S. V.; Barbas, C. F., III. Org. Lett. 2007, 9, 3445. For reviews on the de novo synthesis of carbohydrates, see:
27. (d) Schmidt, R. R. Pure Appl. Chem. 1987, 59, 415.
28. (e) Kirschning, A.; Jesberger, M.; Schoning, K.-U. Synthesis 2001, 507.
29. (f) Vogel, P. In The Organic Chemistry of Sugars; Levy, D. E., Fugedi, P., Eds.; Taylor and Francis Group/CRC Press: Boca Raton, 2006; Chapter 13, p629.
30. (a) Timmer, M. S. M.; Adibekian, A.; Seeberger, P. H. Angew. Chem., Int. Ed. 2005, 44, 7605.
31. (b) Adibekian, A.; Bindschadler, P.; Timmer, M. S. M.; Noti, C; Schutzenmeister, N.; Seeberger, P. H. Chem. Eur. J. 2007, 13, 4510.
32. Kawahara, K.; Sato, N.; Tsuge, K.; Seto, Y. Microbiol. Immunol. 2006, 50, 67.
33. Ndonye, R. M.; Izmirian, D. P.; Dunn, M. F.; Yu, K. O. A.; Porcelli, S. A.; Khurana, A.; Kronenberg, M.; Richardson, S. K.; Howell, A. R. J. Org. Chem. 2005, 70, 10260.
34. Collier, P. N.; Campbell, A. D.; Patel, I.; Raynham, T. M.; Taylor, R. J. K. J. Org. Chem. 2002, 67, 1802.
35. Evans, D. A.; Gage, J. R.; Leighton, J. L.; Kim, A. S. J. Org. Chem. 1992, 57, 1961.
36. (a) Mahrwald, R. Modern Aldol Reactions: Wiley-VCH: Weinheim, 2004.
37. (b) Ager, D. J.; Prakash, I.; Schaad, D. R. Aldrichim. Acta 1997, 30, 3.
38. (a) Evans, D. A.; Bartroli, J.; Shih, T. L. J. Am. Chem. Soc. 1981, 103, 2127.
39. (b) Jones, T. K.; Mills, S. G.; Reamer, R. A.; Askin, D.; Desmond, R.; Volante, R. P.; Shinkai, I. J. Am. Chem. Soc. 1989, 111, 1157.
40. Crimmins, M. T.; King, B. W.; Tabet, E. A.; Chaudhary, K. J. Org. Chem. 2001, 66, 894.
41. (a) Hassner, A.; Strand, G.; Rubinstein, M.; Patchornik, A. J. Am. Chem. Soc. 1975, 97, 1614.
42. (b) van Boom, J. H.; Burgers, P. M. J. Tetrahedron Lett. 1976, 17, 4875.
43. (17)Haigh, D.; Birrell, H. C; Cantello, B. C. C; Hindley, R. M.; Ramaswamy, A.; Rami, H. K.; Stevens, N. C. Tetrahedron: Asymmetry 1999, 10, 1335.
44. Baek, S.; Jo, H.; Kim, H.; Kim, S.; Kim, D. Org. Lett. 2005, 7, 75.
45. (a) Evans, D. A.; Coleman, P. J.; Dias, L. C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2738.
46. (b) Castagner, B.; Leighton, J. L. Tetrahedron 2007, 63, 5895.
47. Altona, C; Haasnoot, C. A. G. Org. Magn. Reson. 1980, 13, 417.
48. Characteristic coupling constants between H-4 and H-5 (J = 1.3 Hz) as well as between H-3 and H-4 (J = 3.4 Hz) unambiguously reveal the desired galacto configuration of building block 5a. NOE correlations between H-5 and H-4 as well as between H-4 and H-3 confirmed the assignment. NOE spectra can be found in the Supporting Information.
49. (a) He, L.; Byun, H. S.; Bittman, R. J. Org. Chem. 2000, 65, 7618.
50. (b) Kolb, H. C; Vannieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
51. 1H NMR analysis.
52. (a) Friestad, G. K.; Marie, J. C; Deveau, A. M. Org. Lett. 2004, 6, 3249.
53. (b) Kloth, K.; Bruenjes, M.; Kunst, E.; Joege, T.; Gallier, F.; Adibekian, A.; Kirschning, A. Adv. Synth. Catal. 2005, 347, 1423.
54. Wulff, G.; Röhle, G. Angew. Chem., Int. Ed. Engl. 1974, 13, 157.
55. (a) Miljkovic, M.; Yeagley, D.; Deslongchamps, P.; Dory, Y. L. J. Org. Chem. 1997, 62, 7597.
56. (b) Demchenko, A. V.; Rousson, E.; Boons, G.-J. Tetrahedron Lett. 1999, 40, 6523.
57. (c) Cheng, Y.-P.; Chen, H.-T.; Lin, C.-C. Tetrahedron Lett. 2002, 43, 7721.
58. Veebham, G. H.; van Leeuven, S. H.; van Boom, J. H. Tetrahedron Lett. 1990, 31, 1331.
59. For α-selective glycosylations with galacturonic acid, see: Nolting, B.; Boye, H.; Vogel, C. J. Carbohydr. Chem. 2000, 19, 923.