Synthesis of the bicyclo[7.3.0]dodecadiyne core of the maduropeptin chromophore

Chemistry - An Asian Journal

Volumn 3, Issue 2, 2008, Pages 447-453

  Iso, Kentaro ^b   Inoue, Masayuki ^a   Kato, Nobuki ^b   Hirama, Masahiro ^b  

^a UNIVERSITY OF TOKYO   (Japan)

^b TOHOKU UNIVERSITY   (Japan)

Author keywords

Alkynes; Antitumor agents; Cyclization; Natural products; Palladium

Indexed keywords

BICYCLO COMPOUND; ENEDIYNE; PEPTIDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

BICYCLO COMPOUNDS; ENEDIYNES; MOLECULAR STRUCTURE; PEPTIDES;

EID: 40149101319     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.200700310     Document Type: Article

References (61)

1. a) N. Zein, W. Solomon, K. L. Colson, D. R. Schroeder, Biochemistry 1995, 34, 11 591-11 597;
2. b) D. R. Schroeder, K. L. Colson, S. E. Klohr, N. Zein, D. R. Langley, M. S. Lee, J. A. Matson, T. W. Doyle, J. Am. Chem. Soc. 1994, 116, 9351-9352;
3. c) M. Hanada, H. Ohkuma, T. Yonemoto, K. Tomita, M. Ohbayashi, H. Kamei, T. Miyaki, M. Konishi, H. Kawaguchi, S. Forenza, J. Antibiot. 1991, 44, 403-414.
4. a) T. Otani, Y. Minami, T. Marunaka, R. Zhang, M.-Y. Xie, J. Antibiot. 1988, 41, 1580-1585;
5. b) Y. Zhen, S. Ming, Y. Bin, T. Otani, H. Saito, Y. Yamada, J. Antibiot. 1989, 42, 1294-1298.
6. a) J. E. Leet, D. R. Schroeder, S. J. Hofstead, J. Golik, K. L. Colson, S. Huang, S. E. Klohr, T. W. Doyle, J. A. Matson, J. Am. Chem. Soc. 1992, 114, 7946-7948;
7. b) S. Kawata, S. Ashizawa, M. Hirama, J. Am. Chem. Soc. 1997, 119, 12 012-12 013.
8. Neocarzinostatin (Eds.: H. Maeda, K. Edo, N. Ishida), Springer, Tokyo, 1997.
9. For a review on chromoprotein antibiotics and other enediyne natural products, see: Z. Xi, I. H. Goldberg in Comprehensive Natural Products Chemistry, Vol. 7 (Eds.: D. H. R. Barton, K. Nakanishi), Elsevier, Amsterdam, 1999, pp. 553-592.
10. For synthetic studies on the maduropeptin chromophore by our research group, see: a) N. Kato, S. Shimamura, Y. Kikai, M. Hirama, Synlett 2004, 2107-2110;
11. b) N. Kato, S. Shimamura, S. Khan, F. Takeda, Y. Kikai, M. Hirama, Tetrahedron 2004, 60, 3161-3172;
12. c) S. Khan, N. Kato, M. Hirama, Synlett 2000, 1494-1496.
13. We recently synthesized the aglycon of the maduropeptin chromophore by using a different strategy: K. Komano, S. Shimamura, M. Inoue, M. Hirama, J. Am. Chem. Soc. 2007, 129, 14 184-14 186.
14. For synthetic studies on the maduropeptin chromophore by other research groups, see: a) W. M. Dai, K. C. Fong, C. W. Lau, L. Zhou, W. Hamaguchi, S. Nishimoto, J. Org. Chem. 1999, 64, 682-683;
15. b) C. Roger, D. S. Grierson, Tetrahedron Lett. 1998, 39, 27-30;
16. c) J. Suffert, D. Toussaint, Tetrahedron Lett. 1997, 38, 5507-5510;
17. d) K. C. Nicolaou, K. Koide, J. Xu, M. H. Izraelewicz, Tetrahedron Lett. 1997, 38, 3671-3674;
18. e) K. C. Nicolaou, K. Koide, Tetrahedron Lett. 1997, 38, 3667-3670;
19. f) P. Magnus, R. Carter, M. Davies, J. Elliott, T. Pitterna, Tetrahedron 1996, 52, 6283-6306.
20. Total syntheses of nine-membered-ring enediynes have been reported; for N-1999-A2, see: a) T. A. Dineen, M. A. Zajac, A. G. Myers, J. Am. Chem. Soc. 2006, 128, 16 406-16 409;
21. b) S. Kobayashi, S. Ashizawa, Y. Takahashi, Y. Sugiura, M. Nagaoka, M. J. Lear, M. Hirama, J. Am. Chem. Soc. 2001, 123, 11 294-11 295;
22. for the neocarzinostatin chromophore, see: c) S. Kobayashi, M. Hori, G. X. Wang, M. Hirama, J. Org. Chem. 2006, 71, 636-644;
23. d) A. G. Myers, R. Glatthar, M. Hammond, P. M. Harrington, E. Y. Kuo, J. Liang, S. E. Schaus, Y. Wu, J.-N. Xiang, J. Am. Chem. Soc. 2002, 124, 5380-5401;
24. e) A. G. Myers, J. Liang, M. Hammond, P. M. Harrington, Y. Wu, E. Y. Kuo, J. Am. Chem. Soc. 1998, 120, 5319-5320;
25. for the proposed structure of kedarcidin, see: f) F. Ren, P. C. Hogan, A. J. Anderson, A. G. Myers, J. Am. Chem. Soc. 2007, 129, 5381-5383.
26. D. B. Dess, J. C. Martin, J. Am. Chem. Soc. 1991, 113, 7277-7287.
27. a) K. Iida, M. Hirama, J. Am. Chem. Soc. 1994, 116, 10310-10311;
28. b) A. G. Myers, P. M. Harrington, E. Y. Kuo, J. Am. Chem. Soc. 1991, 113, 694-695;
29. c) T. Imamoto, Y. Sugiura, N. Takiyama, Tetrahedron Lett. 1984, 25, 4233-4236.
30. a) K. Sonogashira in Comprehensive Organic Synthesis, Vol. 3 (Eds.: B. M. Trost, I. Fleming), Pergamon, London, 1990, pp. 521;
31. b) K. Sonogashira, Y. Tohda, N. Hagiwara, Tetrahedron Lett. 1975, 16, 4467-4470.
32. For reviews on the synthesis of enediyne compounds, see: a) K. C. Nicolaou, W. M. Dai, Angew. Chem. 1991, 103, 1453-1481;
33. Angew. Chem. Int. Ed. Engl. 1991, 30, 1387-1416;
34. b) S. J. Danishefsky, M. D. Shair, J. Org. Chem. 1996, 61, 16-44;
35. c) J. W. Grissom, G. U. Gunawardena, D. Klingberg, D. Huang, Tetrahedron 1996, 52, 6453-6518;
36. d) R. Brückner, J. Suffert, Synlett 1999, 657.
37. For related strategies, see: a) H. Tanaka, H. Yamada, A. Matsuda, T. Takahashi, Synlett 1997, 381-383;
38. b) M. D. Shair, T. Y. Yoon, K. K. Mosny, T. C. Chou, S. J. Danishefksy, J. Am. Chem. Soc. 1996, 118, 9509-9525;
39. c) M. D. Shair, T. Y. Yoon, S. J. Danishefsky, Angew. Chem. 1995, 107, 1883-1885;
40. Angew. Chem. Int. Ed. Engl. 1995, 34, 1721-1723;
41. d) M. D. Shair, T. Y. Yoon, S. J. Danishefsky, J. Org. Chem. 1994, 59, 3755-3757.
42. S. Kawata, M. Hirama, Tetrahedron Lett. 1998, 39, 8707-8710.
43. T. Imamoto, N. Takiyama, K. Nakamura, T. Hatajima, Y. Kamiya, J. Am. Chem. Soc. 1989, 111, 4392-4398.
44. D. L. Comins, A. Dehghani, Tetrahedron Lett.. 1992, 33, 6299-6302.
45. For representative examples of related chemoselective coupling reactions, see: a) D. J. Armitt, G. T. Crisp, Tetrahedron 2006, 62, 1485-1493;
46. b) A. B. Dounay, K. Hatanaka, J. J. Kodanko, M. Oestreich, L. E. Overman, L. A. Pfeifer, M. M. Weiss, J. Am. Chem. Soc. 2003, 125, 6261-6271;
47. c) M. Lu, Y. Pan, Z. Peng, Tetrahedron Lett. 2002, 43, 7903-7906;
48. d) T. Mizutani, S. Honzawa, S. Tosaki, M. Shibasaki, Angew. Chem. 2002, 114, 4874-4876;
49. Angew. Chem. Int. Ed. 2002, 41, 4680-4682;
50. e) A. M. Echavarren, J. K. Stille, J. Am. Chem. Soc. 1987, 109, 5478-5486.
51. a) Q. Liu, D. J. Burton, Tetrahedron Lett. 1997, 38, 4371-4374;
52. b) R. Rossi, A. Carpita, C. Begelli, Tetrahedron Lett. 1985, 26, 523-526;
53. c) A. S. Hay, J. Org. Chem. 1962, 27, 3320-3321;
54. for a review of alkyne coupling, see: d) P. Siemsen, R. C. Livingston, F. Diederich, Angew. Chem. 2000, 112, 2740-2767;
55. Angew. Chem. Int. Ed. 2000, 39, 2632-2657.
56. I-free Sonogashira coupling, see: a) A. Tougerti, S. Negri, A. Jutand, Chem. Eur. J. 2007, 13, 666-676;
57. b) J. H. Li, X. D. Zhang, Y. X. Xie, Eur. J. Org. Chem. 2005, 4256-4259;
58. c) S. Urgaonkar, J. G. Verkade, J. Org. Chem. 2004, 69, 5752-5755;
59. d) A. Soheili, J. Albaneze-Walker, J. A. Murry, P. G. Dormer, D. L. Hughes, Org. Lett. 2003, 5, 4191-4194.
60. In sharp contrast to a bicyclo[7.3.0]dodecatrienediyne core structure of the C-1027 chromophore (M. Inoue, S. Hatano, M. Kodama, T. Sasaki, T. Kikuchi, M. Hirama, Org. Lett. 2004, 6, 3833-3836), compounds 2A and 2B are stable at room temperature.
61. We were unable to determine the configuration of 2A and 2B at C5 despite extensive NMR spectroscopic experiments.