One-pot synthesis of camalexins and 3,3′-biindoles by the Masuda borylation-Suzuki arylation (MBSA) sequence

European Journal of Organic Chemistry

Volumn , Issue 21, 2013, Pages 4564-4569

  Tasch, Boris O A ^a   Antovic, Dragutin ^a   Merkul, Eugen ^a   Müller, Thomas J J ^a  

^a HEINRICH HEINE UNIVERSITY   (Germany)

Author keywords

Alkaloids; Arylation; Boron; C C coupling; Palladium; Synthetic methods

Indexed keywords

EID: 84880004575     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201300133     Document Type: Article

References (60)

1. A. J. Kochanowska-Karamyan, M. T. Hamann, Chem. Rev. 2010, 110, 4489-4497.
2. H. Fan, J. Peng, M. T. Hamann, J.-F. Hu, Chem. Rev. 2008, 108, 264-287;
3. for a minireview on indole alkaloid marine natural products as a source of lead structures in drug development, see, for example:, W. Gul, M. T. Hamann, Life Sci. 2005, 78, 442-453.
4. S. R. Walker, E. J. Carter, B. C. Huff, J. C. Morris, Chem. Rev. 2009, 109, 3080-3098.
5. P. M. Pauletti, L. S. Cintra, C. G. Braguine, A. A. S. Filho, M. L. A. Silva, W. R. Cunha, A. H. Januario, Mar. Drugs 2010, 8, 1526-1549.
6. T. J. J. Müller, Top. Organomet. Chem. 2006, 19, 149-205.
7. A. S. Abreu, P. M. T. Ferreira, M.-J. R. P. Queiroz, I. C. F. R. Ferreira, R. C. Calhelha, L. M. Estevinho, Eur. J. Org. Chem. 2005, 14, 2951-2957.
8. P.-E. Broutin, I. Čerňa, M. Campaniello, F. Leroux, F. Colobert, Org. Lett. 2004, 6, 4419-4422.
9. M. Penhoat, V. Levacher, G. Dupas, J. Org. Chem. 2003, 68, 9517-9520.
10. O. Baudoin, M. Cesario, D. Guénard, F. Guéritte, J. Org. Chem. 2002, 67, 1199-1207.
11. O. Baudoin, D. Guénard, F. Guéritte, J. Org. Chem. 2000, 65, 9268-9271.
12. W. K. Chow, O. Y. Yuen, C. M. So, W. T. Wong, F. Y. Kwong, J. Org. Chem. 2012, 77, 3543-3548.
13. Y. Zhang, J. Gao, W. Li, H. Lee, B. Z. Lu, C. H. Senanayake, J. Org. Chem. 2011, 76, 6394-6400.
14. G. A. Molander, S. L. J. Trice, S. D. Dreher, J. Am. Chem. Soc. 2010, 132, 17701-17703.
15. K. L. Billingsley, T. E. Barder, S. L. Buchwald, Angew. Chem. 2007, 119, 5455; .
16. Angew. Chem. Int. Ed. 2007, 46, 5359-5363
17. W. K. Chow, C. M. So, C. P. Lau, F. Y. Kwong, Chem. Eur. J. 2011, 17, 6913-6917.
18. E. Merkul, E. Schäfer, T. J. J. Müller, Org. Biomol. Chem. 2011, 9, 3139-3141.
19. B. O. A. Tasch, E. Merkul, T. J. J. Müller, Eur. J. Org. Chem. 2011, 24, 4532-4535.
20. M. S. C. Pedras, E. E. Yaya, E. Glawischnig, Nat. Prod. Rep. 2011, 28, 1381-1405.
21. I. Ahuja, R. Kissen, A. M. Bones, Trends Plant Sci. 2012, 17, 1360-1385.
22. For a general review on camalexin, see:, E. Glawischnig, Phytochemistry 2007, 68, 401-406.
23. L. M. Browne, K. L. Conn, W. A. Ayer, J. P. Tewari, Tetrahedron 1991, 47, 3909-3914.
24. J. Tsuji, E. P. Jackson, D. A. Gage, R. Hammerschmidt, S. C. Somerville, Plant Physiol. 1992, 98, 1304-1309.
25. L. D. Jimenez, W. A. Ayer, J. P. Tewari, Phytoprotection 1997, 78, 99-103.
26. M. Zook, L. Leege, D. Jacobson, R. Hammerschmidt, Phytochemistry 1998, 49, 2287-2289.
27. M. S. C. Pedras, Z. Minic, V. K. Sarma-Mamillapalle, J. Agric. Food Chem. 2009, 57, 2429-2435.
28. R. Mezencev, T. Updegrove, P. Kutschy, M. Repovská, J. F. McDonald, J. Nat. Med. 2011, 65, 488-499.
29. R. Mezencev, J. Mojzis, M. Pilatova, P. Kutschy, Neoplasma 2003, 50, 239-245.
30. W. A. Ayer, P. A. Craw, Y. Ma, S. Miao, Tetrahedron 1992, 48, 2919-2924.
31. T. Sakamoto, Y. Kondo, N. Takazawa, H. Yamanaka, J. Chem. Soc. Perkin Trans. 1 1996, 1927-1934.
32. A. Fürstner, A. Ernst, Tetrahedron 1995, 51, 773-786.
33. M. Dzurilla, P. Kutschy, J. Zaletova, M. Ruzinsky, V. Kovacik, Molecules 2001, 6, 716-720.
34. A. R. Hodder, R. J. Capon, J. Nat. Prod. 1991, 54, 1661-1663.
35. R. S. Norton, R. J. Wells, J. Am. Chem. Soc. 1982, 104, 3628-3635.
36. M. Movassaghi, M. A. Schmidt, Angew. Chem. 2007, 119, 3799; .
37. Angew. Chem. Int. Ed. 2007, 46, 3725-3728
38. C.-L. Fang, S. Horne, N. Taylor, R. Rodrigo, J. Am. Chem. Soc. 1994, 116, 9480-9486.
39. B. V. Bertinetti, M. A. Rodriguez, A. M. Godeas, G. M. Cabrera, J. Antibiot. 2010, 63, 681-683.
40. M. D. Carter, M. Hadden, D. F. Weaver, S. M. H. Jacobo, E. Lu, Int. Pat., EWO 125324 A1, 2006.
41. E. Desarbre, J. Bergman, J. Chem. Soc. Perkin Trans. 1 1998, 2009-2016.
42. U. Berens, J. M. Brown, J. Long, R. Seike, Tetrahedron: Asymmetry 1996, 7, 285-292.
43. J. Bergman, N. Eklund, Tetrahedron 1980, 36, 1445-1450.
44. H. A. Duong, S. Chua, P. B. Huleatt, C. L. L. Chai, J. Org. Chem. 2008, 73, 9177-9180.
45. S. P. H. Mee, V. Lee, J. E. Baldwin, A. Cowley, Tetrahedron 2004, 60, 3695-3712.
46. R. Grigg, A. Teasdale, V. Sridharan, Tetrahedron Lett. 1991, 32, 3859-3862.
47. C. Ramesh, V. Kavala, C.-W. Kuo, B. R. Raju, C.-F. Yao, Eur. J. Org. Chem. 2010, 20, 3796-3801.
48. For Masuda borylation with sterically hindered phosphane ligands, see:, K. L. Billingsley, S. L. Buchwald, J. Org. Chem. 2008, 73, 5589-5591 for examples of Suzuki coupling with sterically hindered phosphane ligands, see
49. A. Zapf, A. Ehrentraut, M. Beller, Angew. Chem. 2000, 112, 4315; .
50. Angew. Chem. Int. Ed. 2000, 39, 4153-4155
51. B. Witulski, N. Buschmann, U. Bergsträßer, Tetrahedron 2000, 56, 8473-8480.
52. S. Sakemi, H. H. Sun, J. Org. Chem. 1991, 56, 4304-4306 for the synthesis of nortopsentins, see
53. P. Fresneda, P. Molina, M. A. Sanz, Synlett 2001, 2, 218-221.
54. C. J. Moody, J. R. A. Roffey, ARKIVOC 2000, 3, 393-401.
55. I. Kawasaki, M. Yamashita, S. Ohta, Chem. Pharm. Bull. 1996, 44, 1831-1839.
56. I. Kawasaki, M. Yamashita, S. Ohta, J. Chem. Soc., Chem. Commun. 1994, 18, 2085-2086 for other literature on nortopsentins, see, for example
57. P. Diana, A. Carbone, P. Barraja, A. Montalbano, A. Martorana, G. Dattolo, O. Gia, J. D. Via, G. Cirricione, Bioorg. Med. Chem. Lett. 2007, 17, 2342-2346.
58. F. Y. Miyake, K. Jakushijin, D. A. Horne, Org. Lett. 2000, 2, 2121-2123 for the synthesis of thiazole analogues of nortopsentins, see
59. X.-H. Gu, X.-Z. Wan, B. Jiang, Bioorg. Med. Chem. Lett. 1999, 9, 569-572.
60. For the N-tosylation procedure, see:, K. Mitsudo, P. Thansandote, T. Wilhelm, B. Mariampillai, M. Lautens, Org. Lett. 2006, 8, 3939-3942.