Synthesis of α-s-glycosphingolipids based on uronic acids

Organic Letters

Volumn 13, Issue 19, 2011, Pages 5168-5171

  O'Reilly, Ciaran ^a,b   Murphy, Paul V ^a,b  

^a NATIONAL UNIVERSITY OF IRELAND   (Ireland)

^b UNIVERSITY COLLEGE DUBLIN   (Ireland)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOSPHINGOLIPID; URONIC ACID;

ARTICLE; CELL WALL; CHEMICAL STRUCTURE; CHEMISTRY; SPHINGOMONAS; SYNTHESIS;

CELL WALL; GLYCOSPHINGOLIPIDS; MOLECULAR STRUCTURE; SPHINGOMONAS; URONIC ACIDS;

EID: 80054773637     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol202042h     Document Type: Article

References (31)

1. Mattner, J.; DeBord, K. L.; Ismail, N.; Goff, R. D.; Cantu, C.; Zhou, D.; Saint-Mezard, P.;Wang, V.; Gao, Y.;Hoebe, K.; Schneewind, O.; Walker, D.; Beutler, B.; Teyton, L.; Savage, P.; Bendelac, A. Nature 2005, 434, 525-529.
2. 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, 520-525.
3. Lin, K.-H.; Liang, J.-J.; Huang, W.-I.; Lin-Chu, S.-Y.; Su, C.-Y.; Lee, Y.-L.; Jan, J.-T.; Lin, Y.-L.; Cheng, Y.-S. E.; Wong, C.-H. Antimicrob. Agents Chemother. 2010, 54, 4129-4136.
4. Lia, X.; Fujiob, M.; Imamurab, M.; Wub, D.; Vasana, S.; Wong, C.-H.; Hoa, D. D.; Tsujia, M. Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 13010-13015.
5. Kobayashi, E.;Motoki, K.;Uchida, T.; Fukushima,H.; Koezuka, Y. Oncol. Res. 1995, 7, 529-534.
6. Dere, R. T.; Zhu, X. Org. Lett. 2008, 10, 4641-4644.
7. Blauvelt, M. L.; Khalili, M.; Jaung, W.; Paulsen, J.; Anderson, A. C.; Wilson, S. B.; Howell, A. R. Bioorg. Med. Chem. Lett. 2008, 18, 6374-6376.
8. Pachamuthu, K.; Schmidt, R. R. Chem. Rev. 2006, 106, 160-187.
9. Driguez, H. Chem Bio Chem 2001, 2, 311-318.
10. Pilgrim, W.; Murphy, P. V. Org. Lett. 2009, 11, 939-942.
11. Myers, A. G.; Gleason, J. L.; Yoon, T.; Kung, D. W. J. Am. Chem. Soc. 1997, 119, 656-673.
12. Myers, A. G.; Yoon, T. Tetrahedron Lett. 1995, 36, 9429-9432.
13. Bailey, W. F.; Punzalan, E. R. J. Org. Chem. 1990, 55, 5404-5406.
14. Hoffman, R. V.; Maslouh, N.; Cervantes-Lee, F. J. Org. Chem. 2002, 67, 1045-1056.
15. The Hoffman conditions were used previously in sphinganine synthesis: So, R. C.; Ndonye, R.; Izmirian, D. P.; Richardson, S. K.; Guerrera, R. L.; Howell, A. R. J. Org. Chem. 2004, 69, 3233-3235.
16. Veeresa, G.; Datta., A. Tetrahedron Lett. 1998, 19, 3069-3070.
17. The Grubbs II catalyst was prepared from the Grubbs I catalyst as described previously, see: Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R,. H. Org. Lett. 1999, 1, 953-956.
18. Hanessian, S.; Giroux, S.; Larsson, A. Org. Lett. 2006, 8, 5481-5484.
19. Nicolaou, K. C.; Adsool, V. A.; Hale, C. R. H. Org. Lett. 2010, 12, 1552-1555.
20. Pilgrim, W.; Murphy, P. V. J. Org. Chem. 2010, 75, 6747-6755.
21. Kramer, S.; Nolting B. Ott, A. J.; Vogel, C. J. Carbohydr. Chem. 2000, 19, 891-921.
22. MacDougall, J. M.; Zhang, X. D.; Polgar, W. E.; Khroyan, T. V.; Toll, L.; Cashman, J. R. J. Med. Chem. 2004, 47, 5809-5815.
23. Long, R. M.; Lagisetti, C.; Coates, R. M.; Croteau, R. B. Arch. Biochem. Biophys. 2008, 477, 384-389.
24. Howarth, N. M.; Lindsell, W. E.; Murray, E.; Preston, P. N. Tetrahedron 2005, 61, 8875-8887.
25. Mayato, C; Dorta, R.,L.; Vazquez, J.,T. Tetrahedron Lett. 2008, 49, 1396-1398.
26. Ellervik, U.; Magnussan, G. Tetrahedron Lett. 1997, 38, 1627-1628.
27. Synthesis of the S-glycoside analogue of KRN7000 has been reported but not the S-glycoside of uronic acid derivatives. See refs 6a and 6b.
28. For related publications, see: Poláková, M.; Pitt, N.; Tosin, M.; Murphy, P. V. Angew. Chem., Int. Ed. 2004, 43, 2518-2521.
29. Tosin, M.; Murphy, P. V. Org. Lett. 2002, 4, 3675-78.
30. O'Brien, C.; Poláková, M.; Pitt, N.; Tosin, M.; Murphy, Paul, V. Chem.;Eur. J. 2007, 13, 902-909.
31. See Dere, R. T.; Wang, Y.; Zhu, X. Org. Biomol. Chem. 2008, 6, 2061-2063