Palladium(II)-catalyzed synthesis of the formylcarbazole alkaloids murrayaline A-C, 7-methoxymukonal, and 7-methoxy-o-methylmukonal

European Journal of Organic Chemistry

Volumn 2014, Issue 19, 2014, Pages 4014-4028

  Hesse, Ronny ^a   Krahl, Micha P ^a   Jäger, Anne ^a   Kataeva, Olga ^a   Schmidt, Arndt W ^a   Knölker, Hans Joachim ^a  

^a DRESDEN UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

Alkaloids; C H activation; Cyclization; Natural products; Nitrogen heterocycles; Palladium

Indexed keywords

EID: 84903381615     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201402201     Document Type: Article

References (56)

1. C. J. Moody, Synlett 1994, 681.
2. H.-J. Knölker, K. R. Reddy, Chem. Rev. 2002, 102, 4303.
3. D. P. Chakraborty, S. Roy, in: Progress in the Chemistry of Organic Natural Products, vol. 85 (Eds.:, W. Herz, H. Grisebach, G. W. Kirby, W. Steglich, C. Tamm), Springer-Verlag, Wien, Austria, 2003, p. 125.
4. L. Ackermann, A. Althammer, Angew. Chem. Int. Ed. 2007, 46, 1627;
5. Angew. Chem. 2007, 119, 1652.
6. T. Watanabe, S. Ueda, S. Inuki, S. Oishi, N. Fujii, H. Ohno, Chem. Commun. 2007, 4516.
7. H.-J. Knölker, K. R. Reddy, in: The Alkaloids (Ed.:, G. A. Cordell), Academic Press, Amsterdam, 2008, vol. 65, p. 1.
8. T. A. Choi, R. Czerwonka, R. Forke, A. Jäger, J. Knöll, M. P. Krahl, T. Krause, K. R. Reddy, S. G. Franzblau, H.-J. Knölker, Med. Chem. Res. 2008, 17, 374.
9. H.-J. Knölker, in: Modern Alkaloids (Eds.:, E. Fattorusso, O. Taglialatela-Scafati), Wiley-VCH, Weinheim, Germany, 2008, p. 475.
10. H.-J. Knölker, Chem. Lett. 2009, 38, 8.
11. N. Kongkathip, B. Kongkathip, Heterocycles 2009, 79, 121.
12. K. Thevissen, A. Marchand, P. Chaltin, E. M. K. Meert, B. P. A. Cammue, Curr. Med. Chem. 2009, 16, 2205.
13. R. Forke, K. K. Gruner, K. E. Knott, S. Auschill, S. Agarwal, R. Martin, M. Böhl, S. Richter, G. Tsiavaliaris, R. Fedorov, D. J. Manstein, H. O. Gutzeit, H.-J. Knölker, Pure Appl. Chem. 2010, 82, 1975.
14. K. K. Gruner, H.-J. Knölker, in: Heterocycles in Natural Product Synthesis (Eds.:, K. C. Majumdar, S. K. Chattopadhyay), Wiley-VCH, Weinheim, Germany, 2011, p. 341.
15. T. Nagappan, P. Ramasamy, M. E. A. Wahid, T. C. Segaran, C. S. Vairappan, Molecules 2011, 16, 9651.
16. I. Bauer, H.-J. Knölker, Top. Curr. Chem. 2012, 309, 203.
17. A. W. Schmidt, K. R. Reddy, H.-J. Knölker, Chem. Rev. 2012, 112, 3193.
18. C. Chaichantipyuth, S. Pummangura, K. Naowsaran, D. Thanyavuthi, J. E. Anderson, J. L. McLaughlin, J. Nat. Prod. 1988, 51, 1285.
19. C. Ito, S. Katsuno, H. Ohta, M. Omura, I. Kajiura, H. Furukawa, Chem. Pharm. Bull. 1997, 45, 48.
20. X.-J. Shi, G. Ye, W.-J. Tang, W.-M. Zhao, Helv. Chim. Acta 2010, 93, 985.
21. W. Maneerat, T. Ritthiwigrom, S. Cheenpracha, T. Promgool, K. Yossathera, S. Deachathai, W. Phakhodee, S. Laphookhieo, J. Nat. Prod. 2012, 75, 741.
22. N. Ruangrungsi, J. Ariyaprayoon, G. L. Lange, M. G. Organ, J. Nat. Prod. 1990, 53, 946.
23. T.-S. Wu, S.-C. Huang, P.-L. Wu, C.-S. Kuoh, Phytochemistry 1999, 52, 523.
24. T.-S. Wu, S.-C. Huang, P.-L. Wu, C.-M. Teng, Phytochemistry 1996, 43, 133.
25. A. Sunthitikawinsakul, N. Kongkathip, B. Kongkathip, S. Phonnakhu, J. W. Daly, T. F. Spande, Y. Nimit, S. Rochanaruangrai, Planta Med. 2003, 69, 155.
26. T. Thongthoom, U. Songsiang, C. Phaosiri, C. Yenjai, Arch. Pharmacal Res. 2010, 33, 675.
27. T. Sripisut, S. Cheenpracha, T. Ritthiwigrom, U. Prawat, S. Laphookhieo, Rec. Nat. Prod. 2012, 6, 376.
28. U. Songsiang, T. Thongthoom, P. Zeekpudsa, V. Kukongviriyapan, C. Boonyarat, J. Wangboonskul, C. Yenjai, ScienceAsia 2012, 38, 75.
29. B. Kongkathip, N. Kongkathip, A. Sunthitikawinsakul, C. Napaswat, C. Yoosook, Phytother. Res. 2005, 19, 728.
30. B. Kongkathip, S. Sutthiprabha, C. Yoosook, Y. Mongkolsook, N. Kongkathip, J. Chromatogr. Sci. 2010, 48, 445.
31. O. Kataeva, M. P. Krahl, H.-J. Knölker, Org. Biomol. Chem. 2005, 3, 3099.
32. M. P. Krahl, O. Kataeva, A. W. Schmidt, H.-J. Knölker, Eur. J. Org. Chem. 2013, 59.
33. R. Forke, M. P. Krahl, F. Däbritz, A. Jäger, H.-J. Knölker, Synlett 2008, 1870.
34. H. Furukawa, C. Ito, M. Yogo, T.-S. Wu, Chem. Pharm. Bull. 1986, 34, 2672.
35. C. Ito, M. Nakagawa, T.-S. Wu, H. Furukawa, Chem. Pharm. Bull. 1991, 39, 2525.
36. H.-J. Knölker, N. O'Sullivan, Tetrahedron 1994, 50, 10893.
37. H.-J. Knölker, Curr. Org. Synth. 2004, 1, 309.
38. R. Forke, M. P. Krahl, F. Däbritz, A. Jäger, H.-J. Knölker, Org. Biomol. Chem. 2008, 6, 2481.
39. K. K. Gruner, H.-J. Knölker, Org. Biomol. Chem. 2008, 6, 3902.
40. R. Hesse, A. Jäger, A. W. Schmidt, H.-J. Knölker, Org. Biomol. Chem. 2014, 12,.
41. B. Åkermark, L. Eberson, E. Jonsson, E. Pettersson, J. Org. Chem. 1975, 40, 1365.
42. J. F. Hartwig, Angew. Chem. Int. Ed. 1998, 37, 2046;
43. Angew. Chem. 1998, 110, 2154.
44. A. R. Muci, S. L. Buchwald, Top. Curr. Chem. 2002, 219, 131.
45. M. D. Charles, P. Schultz, S. L. Buchwald, Org. Lett. 2005, 7, 3965.
46. D. S. Surry, S. L. Buchwald, Angew. Chem. Int. Ed. 2008, 47, 6338;
47. Angew. Chem. 2008, 120, 6438.
48. R. Hesse, K. K. Gruner, O. Kataeva, A. W. Schmidt, H.-J. Knölker, Chem. Eur. J. 2013, 19, 14098.
49. T. Gensch, M. Rönnefahrt, R. Czerwonka, A. Jäger, O. Kataeva, I. Bauer, H.-J. Knölker, Chem. Eur. J. 2012, 18, 770.
50. H.-D. Becker, J. Org. Chem. 1965, 30, 982.
51. F. Anwer, A. S. Masaldan, R. S. Kapil, S. P. Popli, Indian J. Chem. 1973, 11, 1314.
52. E. Winterfeldt, Synthesis 1975, 617.
53. G. M. Sheldrick, SHELXS-97, Programs for Crystal Structure Solution, University of Göttingen, Germany, 1997.
54. G. M. Sheldrick, SADABS, v. 2.10, Bruker/Siemens Area Detector Absorption Correction Program, Bruker AXS Inc., Madison, WI, USA, 2002.
55. G. M. Sheldrick, SHELXL-97, Programs for Crystal Structure Refinement, University of Göttingen, Germany, 1997.
56. L. Farrugia, J. Appl. Crystallogr. 1997, 30, 565.