Biomimetic synthesis of 2,5-Bis(indol-3-ylmethyl)pyrazine via intermolecular amino aldehyde cyclization

Synlett

Volumn , Issue 16, 2011, Pages 2339-2342

  Badrinarayanan, Sandhya ^a   Sperry, Jonathan ^a  

^a UNIVERSITY OF AUCKLAND   (New Zealand)

Author keywords

alkaloid; biomimetic; cyclization; pyrazine

Indexed keywords

2,5 BIS(INDOL 3 YLMETHYL)PYRAZINE; AMINOALDEHYDE; PYRAZINE DERIVATIVE; TRYPTOPHAN; UNCLASSIFIED DRUG;

ARTICLE; BIOMIMETICS; BIOSYNTHESIS; CHEMICAL STRUCTURE; CYCLIZATION;

EID: 80053121533     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0030-1260310     Document Type: Article

References (56)

1. Maga J A., Sizer C E., J. Agric. Food Chem. 1973 21 22
2. Arnoldi A, Arnoldi C, Baldi O, Griffini A, [nl] J. Agric. Food Chem. 1988 36 988
3. Sumoto K, Irie M, Mibu N, Miyano S, Nakashima Y, Watanabe K, Yamaguchi T, Chem. Pharm. Bull. 1991 39 792
4. Eitelman S J., Feather M S., Carbohydr. Res. 1979 77 205
5. Candiano G, Ghiggeri G M., Gusmano R, Zetta L, Benfenati E, Icardi G, Carbohydr. Res. 1988 184 67
6. Kerns R J., Tpoida T, Linhardt R J., J. Carbohyr. Chem. 1996 15 581
7. Rohovec J, Kotek J, Peters J A., Maschmeyer T, Eur. J. Org. Chem. 2001 3299
8. For recent examples, see:, Mondal R, Ko S, Bao Z, [nl]J. Mater. Chem. 2010 20 10568
9. Saito R, Matsumura Y, Suzuki S, Okazaki N, Tetrahedron 2010 66 8273
10. Wriedt M, Je I, Nther C, Eur. J. Inorg. Chem. 2009 363
11. Liu H.-Y, Wu H, Ma J.-F, Yang J, Liu Y.-Y, Dalton Trans. 2009 38 7957
12. Goher M A. S., Bitschnau B, Sodin B, Gspan C, Mautner F A., J. Mol. Struct. 2008 886 32
13. Chang S.-Y, Kavitha J, Li [nl]S.-W, Hsu C.-S, Chi Y, Yeh Y.-S, Chou P.-T, Lee [nl]G.-H, Carty A J., Tao Y.-T, Chien C.-H, Inorg. Chem. 2006 45 137
14. Chang C H., Yun M H., Choi W J., Synth. Met. 2004 145 1
15. For selected examples, see:, Bobek M, Bloch A, [nl] J. Med. Chem. 1972 15 164
16. Street L J., Baker R, Book T, Reeve A J., Saunders J, Willson T, Marwood R S., Patel S, Freedman S B., J. Med. Chem. 1992 35 295
17. Seitz L E., Suling W J., Reynolds R C., J. Med. Chem. 2002 45 5604
18. Niculescu-Duvaz I, Roman E, Whittaker S R., Friedlos F, Kirk R, Scanlon I J., Davies L C., Niculescu-Duvaz D, Marais R, Springer [nl]C J., J. Med. Chem. 2008 51 3261
19. Cheng X.-C, Liu [nl]X.-Y, Xu W.-F, Guo X.-L, Zhang N, Song Y.-N, Bioorg. Med. Chem. 2009 17 3018
20. Zitko J, Dolezai M, Svobodova M, Vejsova M, Kucera R, Jilek P, Bioorg. Med. Chem. 2011 19 1471
21. Dubuisson M L. N., Rees J.-F, Brynaert-Merchand J, Mini-Rev. Med. Chem. 2004 4 159
22. Moser B R., J. Nat. Prod. 2008 71 487
23. Lee S, LaCour T G., Fuchs P, Chem. Rev. 2009 109 2275
24. Chill L, Aknin M, Kashman Y, Org. Lett. 2003 14 2433
25. Durn R, Zubía E, Ortega M J., Naranjo S, Salv J, Tetrahedron 1999 55 13225
26. Saito R, Tokita M, Uda K, Ishikawa C, Satoh M, Tetrahedron 2009 65 3019
27. Dunn G, Newbold G T., Spring F S., J. Chem. Soc. 1949 2586
28. Yokotsuka T, Sasaki M, Kikuchi K, Asao Y, Nobuhara A, Nippon Nogeikagaku Kaishi 1967 41 32
29. Sasaki M, Asao Y, Yokotsuka T, Nippon Nogeikagaku Kaishi 1968 42 288
30. Tatsuka K, Tsuchiya S, J. Antibiot. 1972 25 674
31. Tatsuka K, Fujimoto K, Yamashita M, Tsuchiya T, Umeyama S, Umeyama H, J. Antibiot. 1973 26 606
32. Yong W, Gloer J B., Scott J A., Malloch D, J. Nat. Prod. 1995 58 93
33. Bousquet J F., BelhommedeFranqueville H, Kollmann A, Fritz R, Can. J. Bot. 1980 58 2575
34. Devys M, Barbier M, Kollmann A, Bousquet J.-F, Tetrahedron Lett. 1982 23 5409
35. Huang S.-X, Powell E, Rajski S R., Zhao L.-X, Jiang C.-L, Duan Y, Xu W, Shen B, Org. Lett. 2010 12 3525
36. Shaaban M, Maskey R P., Wagner-Döbler I, Laatsch H, J. Nat. Prod. 2002 65 1660
37. Beck H C., Hansen A M., Lauritsen F R., FEMS Microbiol. Lett. 2003 220 67
38. Mahboobi S, Sellmer A, Burgemeister T, Lyssenko A, Schollmeyer D, Monatsh. Chem. 2004 135 333
39. Fruit C, Turck A, Plé N, Mojovic L, Quéguiner G, Tetrahedron 2001 57 9429
40. Buron F, Plé N, Turck A, Queguiner G, J. Org. Chem. 2005 70 2616
41. Charette A B., Focken T, Org. Lett. 2006 8 2985
42. MontserratMartínez M, Sarandeses L A., PérezSestelo J, Tetrahedron Lett. 2007 48 8536
43. Pea-López M, MontserratMartínez M, Sarandeses L A., PérezSestelo J, Org. Lett. 2010 12 852
44. Okada Y, Taguchi H, Yokoi T, Tetrahedron Lett. 1996 37 2249
45. Okada Y, Taguchi H, Yokoi T, Chem. Pharm. Bull. 1996 44 2259
46. Buron F, Turck A, Plé N, Bischoff L, Marsais F, Tetrahedron Lett. 2007 48 4327
47. Ohta A, Kojima A, Saito T, Kobayashi K, Saito H, Wakabayashi K, Honma S, Sakuma C, Aoyagi Y, Heterocycles 1991 32 923
48. Ohta A, Kojima A, Aoyagi Y, Heterocycles 1990 31 1665
49. Candelon N, Shinkaruk S, Bennetau B, Bennetau-Pelissero B, Dumartin M.-L, Deguil M, Babin P, Tetrahedron 2010 66 2463
50. Chaignaud M, Gillaizeau I, Ouhamou N, Coudert G, Tetrahedron 2008 64 8059
51. Nawrath T, Dickschat J S., Kunze B, Schulz S, Chem. Biodiv. 2010 7 2129
52. Tryptophan diketopiperazine is a known natural product called fellutanine A:, Kozlovsky A G., Vinokurova N G., Adanin V M., Burkhardt H.-M D., Grfe U, J. Nat. Prod. 2000 63 698
53. Rodriguez M, Lignon M.-L, Galas M.-C, Fulcrand P, Mendre C, Aumelas A, Laur J, Martinez J, J. Med. Chem. 1987 30 1366
54. Shao Y M., Yang W.-B, Peng H.-P, Hsu M.-F, Tsai K.-C, Kuo T.-H, Wang A H.-J, Liang P.-H, Lin C.-H, Yang A.-S, Wong C.-H, ChemBioChem 2007 8 1654
55. Dyke H, Steel P G., Thomas E J., J. Chem. Soc., Perkin Trans. 1 1989 525
56. Herranz R, Vinuesa S, Pérez C, García-López M T., De Ceballos M L., delRio J, J. Chem. Soc., Perkin Trans. 1 1991 2749