Synthesis of oxa-B-ring analogs of colchicine through Rh-catalyzed intramolecular [5+2] cycloaddition

European Journal of Organic Chemistry

Volumn , Issue 24, 2012, Pages 4501-4507

  Termath, Andreas Ole ^a   Ritter, Stefanie ^a   König, Marcel ^b   Kranz, Darius Paul ^a   Neudörfl, Jörg Martin ^a   Prokop, Aram ^b   Schmalz, Hans Günther ^a  

^a UNIVERSITY OF COLOGNE   (Germany)

^b Children's Hospital   (Germany)

Author keywords

Antitumor agents; Cascade reactions; Cycloaddition; Homogeneous catalysis; Natural products; Ylides

Indexed keywords

EID: 84865042865     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201200677     Document Type: Article

References (57)

1. E. Nogales, S. G. Wolf, K. H. Downing, Nature 1998, 391, 199-203.
2. P. J. Pelletier, J. B. Caventou, Ann. Chim. Phys. 1820, 14, 69-83.
3. O. Boyé, A. Brossi in The Alkaloids (Eds.:, A. Brossi, G. A. Cordell), Academic Press, San Diego, 1992, vol. 41, pp. 125-176.
4. C. LeHello in The Alkaloids (Ed.:, G. A. Cordell), Academic Press, San Diego, 2000, vol. 53, ch. 5. for a comprehensive review on colchicine total syntheses, see
5. T. Graening, H.-G. Schmalz, Angew. Chem. 2004, 116, 3292-3318;
6. Angew. Chem. Int. Ed. 2004, 43, 3230-3256.
7. R. C. Weisenberg, G. G. Borisy, E. W. Taylor, Biochemistry 1968, 7, 4466-4479.
8. S. Bane Hastie, Pharmacol. Ther. 1991, 51, 377-401.
9. A. Brossi, H. J. Yeh, M. Chrzanowska, J. Wolff, E. Hamel, C. M. Lin, F. Quin, M. Sulfness, J. Silverton, Med. Res. Rev. 1988, 8, 77-94.
10. W. E. Dixon, W. Malden, J. Physiol. (London) 1908, 37, 50-76.
11. R. M. Naidus, R. Rodvein, H. Mielke, Arch. Int. Med. 1977, 137, 394-396.
12. Q. Shi, P. Verdier-Pinard, A. Brossi, E. Hamel, A. T. McPhail, K. H. Lee, J. Med. Chem. 1997, 40, 961-966.
13. B. Bhattacharyya, D. Panda, S. Gupta, M. Banerjee, Med. Res. Rev. 2008, 28, 155-183.
14. N. Nicolaus, J. Zapke, P. Riesterer, J.-M. Neudörfl, A. Prokop, H. Oschkinat, H.-G. Schmalz, ChemMedChem 2010, 5, 661-665.
15. E. Hamel, H. H. Ho, G. J. Kang, C. M. Lin, Biochem. Pharmacol. 1988, 37, 2445-2449.
16. B. Bhattacharyya, J. Wolff, Proc. Natl. Acad. Sci. USA 1974, 71, 1134-1140.
17. M. Rosner, H. G. Capraro, A. E. Jacobsen, L. Atwell, A. Brossi, M. A. Iorio, T. H. Williams, R. H. Sik, C. F. Chignell, J. Med. Chem. 1981, 24, 257-261.
18. G. G. Choudhury, A. Banerjee, B. Bhattacharyya, B. B. Biswas, FEBS Lett. 1983, 161, 55-59.
19. B. Bhattacharyya, J. Wolff, J. Biol. Chem. 1984, 259, 11836-11843.
20. S. B. Hastie, R. C. Williams Jr., D. Puett, T. L. McDonald, J. Biol. Chem. 1989, 264, 6682-6688 for a publication dealing with colchicide, see
21. C. Dumortier, Q. Yan, S. Bane, Y. Engelborghs, Biochem. J. 1997, 327, 685-688 for publications dealing with thiocolchicine, see
22. L. Velluz, G. Müller, Bull. Soc. Chim. Fr. 1954, 755-757.
23. L. Velluz, G. Müller, Bull. Soc. Chim. Fr. 1954, 1072-1075.
24. S. B. Hastie, Biochemistry 1989, 28, 7753-7760.
25. U. Berg, J. Deinum, P. Lincoln, J. Kvassman, Bioorg. Chem. 1991, 19, 53-65.
26. G. Chakrabarti, S. Sengupta, B. Bhattacharyya, J. Biol. Chem. 1996, 271, 2897-2901.
27. A. R. Chaudhuri, P. Seetharamalu, P. M. Schwarz, F. H. Hausheer, R. F. Ludueña, J. Mol. Biol. 2000, 303, 679-692.
28. B. Danieli, G. Lesma, D. Passarella, D. Prosperi, A. Sacchetti, A. Silvani, R. Destro, E. May, E. Bombardelli, Helv. Chim. Acta 2003, 86, 2082.
29. B. Bhattach, J. Wolff, Proc. Natl. Acad. Sci. USA 1974, 71, 2627.
30. T. Graening, W. Friedrichsen, J. Lex, H.-G. Schmalz, Angew. Chem. 2002, 114, 1594-1597;
31. Angew. Chem. Int. Ed. 2002, 41, 1524-1526.
32. T. Graening, V. Bette, J. Neudörfl, J. Lex, H.-G. Schmalz, Org. Lett. 2005, 7, 4317-4320.
33. A. Padwa, G. E. Fryxell, L. Zhi, J. Am. Chem. Soc. 1990, 112, 3100-3109.
34. A. Padwa, R. L. Chinn, S. F. Hornbuckle, Z. J. Zhang, J. Org. Chem. 1991, 56, 3271-3278.
35. A. Padwa, M. D. Weingarten, Chem. Rev. 1996, 96, 223-269.
36. A. Padwa, Helv. Chim. Acta 2005, 88, 1357-1374.
37. For a related temperature effect on a [3+2] cyclization, see:, A. Gromov, V. Enev, J. Mulzer, Tetrahedron Lett. 2009, 50, 5283-5284.
38. D. E. Janssen, C. V. Wilson, Org. Synth. 1956, 36, 46.
39. J. K. Stille, Angew. Chem. 1986, 98, 504-519;
40. Angew. Chem. Int. Ed. Engl. 1986, 25, 508-524.
41. [13a,14]). Their formation can be understood in terms of a [1,4] sigmatropic H-shift:, A. C. Lottes, J. A. Landgrebe, K. Larsen, Tetrahedron Lett. 1989, 30, 4089-4092.
42. E. J. Corey, R. K. Bakshi, S. Shibata, J. Am. Chem. Soc. 1987, 109, 5551-5553.
43. E. J. Corey, R. K. Bakshi, S. Shibata, C. P. Chen, V. K. Singh, J. Am. Chem. Soc. 1987, 109, 7925-7926.
44. E. J. Corey, C. J. Helal, Angew. Chem. 1998, 110, 2092-2118;
45. Angew. Chem. Int. Ed. 1998, 37, 1986-2012.
46. A. Krasovskiy, P. Knochel, Angew. Chem. 2004, 116, 3396-3399;
47. Angew. Chem. Int. Ed. 2004, 43, 3333-3336.
48. O. Baron, P. Knochel, Angew. Chem. 2005, 117, 3193-3195;
49. Angew. Chem. Int. Ed. 2005, 44, 3133-3135.
50. K. C. Nicolaou, T. Montagnon, P. S. Baran, Y.-L. Zhong, J. Am. Chem. Soc. 2002, 124, 2245-2258.
51. For some recent publications on 6-oxaallocolchicine derivatives, see:, N. Nicolaus, S. Strauss, J.-M. Neudörfl, A. Prokop, H.-G. Schmalz, Org. Lett. 2009, 11, 341-344.
52. L. Keller, P. Dauban, J. Med. Chem. 2008, 51, 3414-3421.
53. W. H. Habig, M. J. Pabst, W. B. Jakoby, J. Biol. Chem. 1974, 249, 7130-7139.
54. W. H. Ang, L. J. Parker, A. De Luca, L. Juillerat-Jeanneret, C. J. Morton, M. Lo Bello, M. W. Parker, P. J. Dyson, Angew. Chem. 2009, 121, 3912-3915; for a review on GST, see .
55. Angew. Chem. Int. Ed. 2009, 48, 3854-3857
56. J. D. Hayes, J. U. Flanagan, I. R. Jowsey, Annu. Rev. Pharmacol. Toxicol. 2005, 45, 51-88.
57. CCDC-881272 (for the 3,5-dinitrobenzoate of 17), -CCDC-881273 (for 3), and -CCDC-881274 (for ent- 23) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.