Synthesis of novel allocolchicine analogues with a pyridine c-ring through intermolecular vollhardt diyne-nitrile cyclotrimerization

Synlett

Volumn , Issue 14, 2010, Pages 2071-2074

  Nicolaus, Norman ^a   Schmalz, Hans Günther ^a  

^a UNIVERSITY OF COLOGNE   (Germany)

Author keywords

cycloaddition; heterocycles; microwave; natural product analogues; regioselectivity; transition metal catalysis

Indexed keywords

ACETOPHENONE DERIVATIVE; ALKYNE DERIVATIVE; ALLOCOLCHICINE; ALLOCOLCHICINOID DERIVATIVE; ANTINEOPLASTIC AGENT; BENZALDEHYDE DERIVATIVE; COBALT; COLCHICINE; N ACETYL COLCHINOL; NITRILE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CONTROLLED STUDY; CYCLIZATION; CYCLOADDITION; DRUG SYNTHESIS; MOLECULAR INTERACTION; OLIGOMERIZATION; QUANTUM YIELD; RACEMIC MIXTURE; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

EID: 77956052516     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0030-1258512     Document Type: Article

References (38)

1. Capraro H G., Brossi A, In The Alkaloids Vol. 23 Brossi A Academic Press Orlando 1984 Chap. 1
2. Boyé O, Brossi A, In The Alkaloids Vol. 41 Brossi A Cordell G A. Academic Press San Diego 1992 Chap. 3
3. LeHello C, In The Alkaloids Vol. 53 Cordell G A. Academic Press San Diego 2000 Chap. 5
4. Davis P D., Dougherty G J., Blakey D C., Galbraith S M., Tozer G M., Holder A L., Naylor M A., Nolan J, Stratford M R. L., Chaplin D J., Hill S A., Cancer Res. 2002 62 7247
5. Jordan M A., Wilson L, Nat. Rev. Cancer 2004 4 253
6. Tozer G M., Kanthou C, Baguley B C., Nat. Rev. Cancer 2005 5 423
7. For selected examples on recent synthetic work in the field of allocolchicinoids, see:, Vorogushin A V., Predeus [nl]A V., Wulff W D., Hansen H.-J, J. Org. Chem. 2003 68 5826
8. Bergemann S, Brecht R, Büttner F, Guénard D, Gust R, Seitz G, Strubbs M T., Thoret S, Bioorg. Med. Chem. 2003 11 1269
9. Büttner F, Bergemann S, Guénard D, Gust R, Seitz G, Thoret S, Bioorg. Med. Chem. 2005 13 3497
10. LeBlanc M, Fagnou K, Org. Lett. 2005 7 2849
11. Besong G, Jarowicki K, Kocienski P J., Sliwinski E, Boyle F T., Org. Biomol. Chem. 2006 4 2193
12. Djurdjevic S, Green J R., Org. Lett. 2007 9 5505
13. Boyer F.-D, Hanna I, Org. Lett. 2007 9 715
14. Joncour A, Décor A, Liu J.-M, TranHuuDau M.-E, Baudoin O, Chem. Eur. J. 2007 13 5450
15. Joncour A, Liu J.-M, Décor A, Thoret S, Wdzieczak-Bakala J, Bignon J, Baudoin O, ChemMedChem 2008 3 1731
16. Graening T, Friedrichsen W, Lex J, Schmalz H.-G, Angew. Chem. Int. Ed. 2002 41 1524
17. Graening T, Bette V, Neudörfl J, Lex J, Schmalz H.-G, Org. Lett. 2005 7 4317
18. Graening T, Schmalz H.-G, Angew. Chem. Int. Ed. 2004 43 3230
19. Nicolaus N, Zapke J, Riesterer P, Neudörfl J.-M, Prokop A, Oschkinat H, Schmalz H.-G, ChemMedChem 2010 5 661
20. Nicolaus N, Strau S, Neudörfl J.-M, Prokop A, Schmalz H.-G, Org. Lett. 2009 11 341
21. For selected references, see:, Vollhardt K P. C., Bergman R G., J. Am. Chem. Soc. 1974 96 4996
22. Naiman A, Vollhardt K P. C., Angew. Chem. Int. Ed. 1977 16 708
23. Bönnemann H, Angew. Chem. Int. Ed. 1978 17 505
24. Vollhardt K P. C., Angew. Chem. Int. Ed. 1984 23 539
25. Heller B, Sundermann B, Buschmann H, Drexler H.-J, You J, Holzgrabe U, Heller E, Oehme G, J. Org. Chem. 2002 67 4414
26. Varela J A., Saá C, Chem. Rev. 2003 103 3787
27. Gutnov A, Heller B, Fischer C, Drexler H.-J, Spannenberg A, Sundermann B, Sundermann C, Angew. Chem. Int. Ed. 2004 43 3795
28. Zhou Y, Porco J A. Jr., Snyder J K., Org. Lett. 2007 9 393
29. Young D D., Deiters A, Angew. Chem. Int. Ed. 2007 46 5187
30. Heller B, Hapke M, Chem. Soc. Rev. 2007 36 1085
31. Turek P, Hocek M, Pohl R, Klepetáová B, Kotora M, Eur. J. Org. Chem. 2008 3335
32. Geny A, Agnet N, Iannazzo L, Malacria M, Aubert C, Gandon V, Angew. Chem. 2009 121 1842
33. Meiner A, Groth U, Synlett 2010 1051
34. Agenet N, Buisine O, Slowinski F, Gandon V, Aubert C, Malacria M, In Organic Reactions Vol. 68 Overman L Wiley New Jersey 2007 1
35. Kase K, Goswami A, Ohtaki K, Tanabe E, Saino N, Okamoto S, Org. Lett. 2007 9 931
36. For a regioselective cyclotrimerization using a silicon tether, see:, Groth U, Huhn T, Kesenheimer C, Kalogerakis A, Synlett 2005 1758
37. Bonaga L V. R., Zhang H.-C, Maryanoff B E., Chem. Commun. 2004 2394
38. Chopade P R., Louie J, Adv. Synth. Catal. 2006 348 2307