Total synthesis of (+)-batzelladine A and (-)-batzelladine D, and identification of their target protein

Chemistry - A European Journal

Volumn 11, Issue 23, 2005, Pages 6878-6888

  Shimokawa, Jun ^b   Ishiwata, Takanori ^c   Shirai, Koji ^a   Koshino, Hiroyuki ^c   Tanatani, Aya ^b   Nakata, Tadashi ^c,d   Hashimoto, Yuichi ^b   Nagasawa, Kazuo ^a  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

^b UNIVERSITY OF TOKYO   (Japan)

^c INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

^d TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

Batzelladine; Guanidine; Inhibitors; Natural products; Total synthesis

Indexed keywords

INHIBITORS; NATURAL PRODUCTS; TOTAL SYNTHESIS;

COMPLEXATION; PROTEINS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

ORGANOMETALLICS;

ALKALOID; BATZELLADINE A; BATZELLADINE D; GUANIDINE DERIVATIVE; PROTEIN; PYRIMIDINE DERIVATIVE;

CHEMISTRY; CONFERENCE PAPER; FAST ATOM BOMBARDMENT MASS SPECTROMETRY; INFRARED SPECTROPHOTOMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; SYNTHESIS;

ALKALOIDS; GUANIDINES; MAGNETIC RESONANCE SPECTROSCOPY; PROTEINS; PYRIMIDINES; SPECTROMETRY, MASS, FAST ATOM BOMBARDMENT; SPECTROPHOTOMETRY, INFRARED; STEREOISOMERISM;

EID: 27944508218     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200500852     Document Type: Conference Paper

References (47)

1. a) A. D. Patil, N. V. Kumar, W. C. Kokke, M. F. Bean, A. J. Freyer, J. C. De Brosse, S. Mai, A. Truneh, D. J. Faulkner, B. Carté, A. L. Breen, R. P. Hertzberg, R. K. Johnson, J. W. Westley, B. C. M. Potts, J. Org. Chem. 1995, 60, 1182-1188;
2. b) A. D. Patil, A. J. Freyer, P. B. Taylor, B. Carté, G. Zuber, R. K. Johnson, D. J. Faulkner, J. Org. Chem. 1997, 62, 1814-1819.
3. The identification of the source of these compounds was revised: a) R. W. M. Van Soest, J. C. Braekman, D. J. Faulkner, E. Hajdu, M. K. Harper, J. Vacelet, Bull. Inst. R. Sci. Nat. Belg. 1996. 66, 89-102;
4. b) J. C. Braekman, D. Daloze, R. Tavares, E. Hajdu, R. W. M. Van Soest, J. Nat. Prod. 2000, 63, 193-196.
5. a) B. B. Snider, J. Chen, A. D. Patil, A. J. Freyer, Tetrahedron Lett. 1996, 37, 6977-6980;
6. b) B. B. Snider, J. Chen, Tetrahedron Lett. 1998, 59, 5697-5700.
7. a) G. P. Black, P. J. Murphy, N. D. A. Walshe, D. E. Hibbs, M. B. Hursthouse, K. M. A. Malik, Tetrahedron Lett. 1996, 37, 6943-6946;
8. b) G. P. Black, P. J. Murphy, N. D. A. Walshe, Tetrahedron 1998, 54, 9481-9488;
9. c) G. P. Black, P. J. Murphy, A. J. Thornhill, N. D. A. Walshe, C. Zanetti, Tetrahedron 1999, 55, 6547-6554.
10. F. Cohen, L. E. Overman, S. K. L. Sakata, Org. Lett. 1999, 1, 2169-2172.
11. F. Cohen, L. E. Overman, J. Am. Chem. Soc. 2001, 123, 10782-10783.
12. M. A. Arnold, S. G. Duron, D. Y. Gin, J. Am. Chem. Soc. 2005, 127, 6924-6925.
13. A. V. R. Rao, M. K. Gurjar, J. Vasudevan, J. Chem. Soc. Chem. Commun. 1995, 1369-1370.
14. S. Louwrier, M. Ostendorf, A. Tuynman, H. Hiemstra, Tetrahedron Lett. 1996, 37, 905-908.
15. S. G. Duron, D. Y. Gin, Org. Lett. 2001, 3, 1551-1554.
16. P. A. Evans, T. Manangan, Tetrahedron Lett. 2001, 42, 6637-6640.
17. a) M. C. Elliott, M. S. Long, Tetrahedron Lett. 2002, 43, 9191-9194;
18. b) M. C. Elliott, M. S. Long, Org. Biomol. Chem. 2004, 2, 2003-2011.
19. K. Nagasawa, H. Koshino, T. Nakata, Tetrahedron Lett. 2001, 42, 4155-4158.
20. A. Olszewski, K. Sato, Z. D. Aron, F. Cohen, A. Harris, B. R. McDougall, W. E. Jr Robinson, L. E. Overman, G. A. Weiss, Proc. Natl. Acad. Sci. USA 2004, 101, 14079-14084.
21. P. L. Toogood, J. Med. Chem. 2002, 45, 1543-1558.
22. T. Ishiwata, T. Hino, H. Koshino, Y. Hashimoto, T. Nakata, K. Nagasawa, Org. Lett. 2002, 4, 2921-2924.
23. J. Shimokawa, K. Shirai, A. Tanatani, Y. Hashimoto, K. Nagasawa, Angew. Chem. 2004, 116, 1585-1588;
24. Angew. Chem. Int. Ed. 2004, 43, 1559-1562.
25. a) J. J. Tufariello, G.B. Mullen, J. J. Tegeler, E. J. Trybulski, S. C. Wong, Sk. A. Ali, J. Am. Chem. Soc. 1979, 101, 2435-2442;
26. b) J. J. Tufariello, J. M. Puglis, Tetrahedron Lett. 1986, 27, 1489-1492;
27. c) Sk. A. Ali, M. I. M. Wazeer, Tetrahedron Lett. 1993, 34, 137-144.
28. a) K. S. Kim, L. Qian, Tetrahedron Lett. 1993, 34, 7677-7680;
29. b) E. I. Iwanowicz, M. A. Poss, J. Lin, Synth. Commun. 1993, 23, 1443-1445.
30. D. S. Dodd, A. P. Kozikowski, Tetrahedron Lett. 1994, 35, 977-980.
31. I. J. McAlpine, R. W. Armstrong, Tetrahedron Lett. 2000, 41, 1849-1853.
32. K. Nagasawa, T. Ishiwata, Y. Hashimoto, T. Nakata, Tetrahedron Lett. 2002, 43, 6383-6385.
33. A. S. Franklin, S. K. Ly, G. H. Mackin, L. E. Overman, A. J. Shaka, J. Org. Chem. 1999, 64, 1512-1519.
34. J. Xiang, S. Toyoshima, A. Orita, J. Otera, Angew. Chem. 2001, 113, 3782-3784;
35. Angew. Chem. Int. Ed. 2001, 40, 3670-3672.
36. A. Goti, M. Cacciarini, F. Cardona, A. Brandi, Tetrahedron Lett. 1999, 40, 2853-2856.
37. D. H. R. Barton, S. W. McCombie, J. Chem. Soc. Perkin Trans. 1 1975, 1574.
38. K. B. Sharpless, R. F. Lauer, A. Y. Teranishi, J. Am. Chem. Soc. 1973, 95, 6137-6139.
39. a) Y. Ito, T. Hirao, T. Saegusa, J. Org. Chem. 1978, 43, 1011-1013;
40. b) J. Tsuji, I. Minani, I. Shimizu, Tetrahedron Lett. 1983, 24, 5635-5638;
41. c) I. Minani, K. Takahashi, I. Shimizu, T. Kimura, J. Tsuji, Tetrahedron 1986, 42, 2971-2977.
42. K. C. Nicolaou, Y.-L. Zhong, P. S. Baran, J. Am. Chem. Soc. 2000, 122, 7596-7597.
43. S. V. Ley, J. Norman, W. P. Griffith, S. P. Marsden, Synthesis, 1994, 639-666.
44. S. Murahashi, N. Komiya, H. Terai, T. Nakae, J. Am. Chem. Soc. 2003, 125, 15312-15313.
45. a) G. A. Kraus, M. J. Taschner, J. Org. Chem. 1980, 45, 1175-1176;
46. b) G. A. Kraus, B. Roth, J. Org. Chem. 1980, 45, 4825-4830.
47. C. A. Bewley, S. Ray, F. Cohen, S. K. Collins, L. E. Overman, J. Nat. Prod. 2004, 67, 1319-1324.