Synthesis of 'molecular asterisks' via sequential cross-metathesis, sonogashira and cyclotrimerization reactions

Synthesis

Volumn , Issue 6, 2000, Pages 862-868

  Dominique, Romyr ^a   Liu, Bingcan ^a   Das, Sanjoy K ^a   Roy, René ^a  

^a UNIVERSITY OF OTTAWA   (Canada)

Author keywords

Carbohydrates; Cross metathesis; Cyclotrimerization; Glycopeptides; Ruthenium; Sonogashira reaction

Indexed keywords

AMIDATION; ARTICLE; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; SYNTHESIS;

EID: 0034125768     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2000-6266     Document Type: Article

References (40)

1. (a) Grubbs, R. H. In Comprehensive Organometallic Chemistry, Wilkenson, G.; Stone, G. A.; Abel, E. W., Eds.; Pergamon: New York, 1982, Vol. 8, p 499.
2. (b) Feldman, J.; Schrock, R. R. Prog. Inorg. Chem. 1991, 39, 2.
3. (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446.
4. (b) Schrock, R. R. Acc. Chem. Res. 1990, 23, 158.
5. For recent reviews, see: (a) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036.
6. (b) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
7. Armstrong, S. K. J. Chem. Soc., Perkin Trans. I 1998, 371.
8. (a) Schrock, R. R.; Murdzek, J. S.; Bazan, G. C.; Robbins, J.; Dimare, M.; O'Regan. M. J. Am. Chem. Soc. 1990, 112, 3875.
9. (b) Bazan, G. C. Khosravi, E.; Schrock, R. R.; Feast, W. J.; Gibson, V. C.; O'Regan, M. B.; Thomas, J. K.; Davis, W. M. J. Am. Chem. Soc. 1990, 112, 8378.
10. Schwab, P.; France, M. B.; Ziler, J. W.; Grubbs, R. H. Angew. Chem. Int. Ed. Engl. 1995, 34, 2039.
11. (a) Biagini, S. C. G.; Gibson, S. E.; Keen, S. P. J. Chem. Soc., Perkin Trans. I 1998, 2485.
12. (b) Brummer, O.; Ruckert, A.; Blechert, S. Chem. Ear. J. 1997, 3, 441.
13. (c) Blackwell, H. E.; O'Leary, D. J.; Chatterjee, A. K.; Washenfelder, R. A.; Bussmann, D. A.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 58.
14. For a recent review, see: Roy, R.; Das, S. K. Chem. Commun. 2000, 519.
15. (a) Huwe, C. M.; Blechert, S. Tetrahedron Lett. 1995, 36, 1621.
16. (b) Ovaa, H.; Codée, J. D. C.; Lastdrager, B.; Overkleeft, H. S.; van der Marel, G. A.; van Boom, J. H. Tetrahedron Lett. 1999, 40, 5063.
17. (a) Feng, J.; Schuster, M.; Blechert, S. Synlett 1997, 129.
18. (b) O'Leary, D. J.; Blackwell, H. E.; Washenfelder, R. A.; Grubbs, R. H. Tetrahedron Lett. 1998, 39, 7427.
19. (a) Nomura, K.; Schrock, R. R. Macromolecules 1996, 29, 540.
20. (b) Fraser, C.; Grubbs, R. H. Macromolecules 1995, 28, 7248.
21. (c) Kanai, M.; Mortell, K. H.; Kiessling, L. L. J. Am. Chem. Soc. 1997, 119, 9931.
22. (a) Dominique. R.; Das, S. K. Roy, R. J. Chem. Soc.,Chem. Commun. 1998, 2437.
23. (b) Das, S. K.; Dominique, R.; Smith, C.; Nahra, J.; Roy, R. Carbohydr. Lett. 2000, 3, 361.
24. Roy, R.; Dominique, R.; Das, S. K. J. Org. Chem. 1999, 64, 5408.
25. Das, S. K.; Roy, R. Tetrahedron Lett. 1999, 40, 4015.
26. Roy, R.; Das, S. K.; Dominique. R.; Trono, M. C.; Hernandez-Mateo, F.; Santoyo-Gonzalez, F. Pure Appl. Chem. 1999, 71, 565.
27. Du, Y.; Linhardt, R. J.; Vlahou, I. R. Tetrahedron 1998, 54, 9913.
28. Lewis, M. D.; Cha, J. K.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 4976.
29. Bischofberger, N.; Waldmann, H.; Saito, T.; Simon, E. S.; Lees, W.; Bednarski, M. D.; Whitesides, G. M. J. Org. Chem. 1988, 53, 3457.
30. Hosomi, A.; Sakata, Y.; Sukurai, H. Carbohydr. Res. 1987, 171, 223.
31. Giannis, A.; Sandhoff, K. Tetrahedron Lett. 1985, 26, 1479.
32. Perbenzoylated allyl α-D-mannopyranoside was prepared from the corresponding acetate derivative. Since α and β anomers of peracetylated allyl D-mannopyranoside were not separated by silica gel column chromatography, perbenzoylated allyl α,β-D-mannopyranoside was prepared by deacetylation and benzoylation. Allyl perbenzoylated α-D-mannopyranoside and β-D-mannopyranoside were separated by simple silica gel column chromatography.
33. Crowe, W. E.; Goldberg, D. R. J. Am. Chem. Soc. 1995, 117, 5162.
34. Fraser-Reid, B.; Udolong, U. E.; Wu, Z.; Ottosson, H.; Merritt, J. R.; Rao, C. S.; Madsen, R. Synlett 1992, 927.
35. Roy, R. Curr. Opin. Stuct. Biol. 1996, 6, 692, and refernces cited therein.
36. Debenham, S. D.; Debenham, J. S.; Burk, M. J.; Toone, E. J. J. Am. Chem. Soc. 1997, 119, 9897, and references cited therein.
37. Roy, R. Top. Curr. Chem. 1997, 187, 241, and references cited therein.
38. Roy, R.; Das, S. K.; Santoyo-Gonzalez, F.; Hernandez-Mateo, F.; Dam, T. K.; Brewer, C. F. Chem. Eur. J. 2000, in Press.
39. (a) Kaufman, R. J.; Sidhu, R. S. J. Org. Chem. 1982, 47, 4941.
40. (b) Trono, M. C.; Das, S. K.; Roy, R. unpublished results.