A short route for the synthesis of "sweet" macrocycles via a click-dimerization-ring-closing metathesis approach

Chemical Communications

Volumn , Issue 22, 2005, Pages 2852-2854

  Dörner, Simon ^a   Westermann, Bernhard ^a  

^a LEIBNIZ INSTITUTE OF PLANT BIOCHEMISTRY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

LACTONE; MACROCYCLIC COMPOUND;

ANALYTIC METHOD; ARTICLE; DIMERIZATION; METHODOLOGY; REACTION ANALYSIS; RELIABILITY; RING CLOSING METATHESIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 21344450055     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b502682b     Document Type: Article

References (26)

1. J. Furukawa and N. Sakairi, Trends Glycosci. Glycotechnol., 2001, 13, 1;
2. L. A. Wessjohann, E. Ruijter, D. Garcia-Rivera and W. Brandt, Mol. Diversity, 2005, 9, 171.
3. A. Fürstner, Eur. J. Org. Chem., 2004, 943;
4. A. Fürstner and T. Müller, J. Org. Chem., 1998, 63, 424;
5. A. Fürstner and T. Müller, J. Am. Chem. Soc., 1999, 121, 7814.
6. G. W. Chen and A. Kirschning, Chem. Eur. J., 2002, 8, 2717;
7. J. Jaunzems, B. Oelze and A. Kirschning, Org. Biomol. Chem., 2004, 2, 3448;
8. A. Kirschning, G. W. Chen, J. Jaunzems, M. Jesberger, M. Kalesse and M. Lindner, Tetrahedron, 2004, 60, 3505.
9. T. Velasco-Torrijos and P. V. Murphy, Org. Lett., 2004, 6, 3961.
10. M. A. Leeuwenburgh, G. A. van der Marel and H. S. Overkleeft, Curr. Opin. Chem Biol., 2003, 7, 757;
11. G. T. Fan, T. S. Hus, C, C. Lin and C. C. Lin, Tetrahedron Lett., 2000, 41, 6593.
12. H. C. Kolb, M. G. Finn and K. B. Sharpless, Angew. Chem. Int. Ed., 2001, 40, 2004;
13. H. C. Kolb and K. B. Sharpless, Drug Discovery Today, 2003, 8, 1128;
14. C. W. Tornoe, C. Christensen and M. Meldal, J. Org. Chem., 2002, 67, 3057.
15. J. M. Casas-Solvas, A. Vargas-Berenguel, L. F. Capitan-Vallvey and F. Santoyo-Gonzalez, Org. Lett., 2004, 6, 3687;
16. B. H. M. Kuijpers, S. Groothuys, A. R. Keereweer, P. J. L. M. Quaedflieg, R. H. Blaauw, F. L. van Delft and F. P. J. T. Rutjes, Org. Lett., 2004, 6, 3123;
17. F. Perez-Balderas, M. Ortega-Munoz, J. Morales-Sanfrutos, F. Hernandez-Mateo, F. G. Calvo-Flores, J. A. Calvo-Asin, J. Isac-Garcia and F. Santoyo-Gonzalez, Org. Lett., 2003, 5, 1951.
18. R. Tona, R. Bertolini and J. Hunziker, Org. Lett., 2000, 2, 1693.
19. B. Westermann and S. Dörner, Chem. Commun., 2005, 2116;
20. phase transfer conditions for the substitution of anomeric halogens with sodium azide: H. Waldmann, J. März and H. Kunz, Carbohydr. Res., 1990, 196, 75;
21. H. Kunz, H. Waldmann and J. März, Liebigs Ann. Chem., 1989, 45;
22. H. Kunz and H. Waldmann, Angew. Chem., Int. Ed. Engl., 1985, 24, 883.
23. J. R. Cui and D. Horton, Carbohydr. Res., 1998, 309, 319;
24. B. A. Roe, C. G. Boojamra, J. L. Griggs and C. R. Bertozzi, J. Org. Chem., 1996, 61, 6442.
25. B. Elchert, J. Li, J. H. Wang, Y. Hui, R. Rai, R. Ptak, P. Ward, J. Y. Takemoto, M. Bensaci and C. W. T. Chang, J. Org. Chem., 2004, 69, 1513.
26. C. Rosenbohm, D. Van den Berghe, A. Vlietinck and J. Wengel, Tetrahedron, 2001, 57, 6277.