Total synthesis and determination of the absolute configuration of guadinomines B and C2

Chemistry - A European Journal

Volumn 14, Issue 27, 2008, Pages 8220-8238

  Hirose, Tomoyasu ^a   Sunazuka, Toshiaki ^a   Tsuchiya, Satoshi ^a   Tanaka, Toshiaki ^a   Kojima, Yasuhiro ^a   Mori, Ryuma ^a   Iwatsuki, Masato ^a   Õmura, Satoshi ^a  

^a KITASATO UNIVERSITY   (Japan)

Author keywords

Configuration determination; Guadinomines; Natural products; Total synthesis; Type III secretion system

Indexed keywords

BACTERIOLOGY; ONTOLOGY; RAW MATERIALS;

CONFIGURATION DETERMINATION; GUADINOMINES; NATURAL PRODUCTS; TOTAL SYNTHESIS; TYPE III SECRETION SYSTEM;

COMPLEXATION;

DIPEPTIDE; GUADINOMINE B; GUADINOMINE C2; IMIDAZOLIDINE DERIVATIVE;

ARTICLE; CHEMISTRY; CONFORMATION; CYCLIZATION; DOSE RESPONSE; DRUG DESIGN; DRUG EFFECT; ESCHERICHIA COLI; HEMOLYSIS; METHODOLOGY; MICROBIOLOGICAL EXAMINATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STANDARD; STEREOISOMERISM; SYNTHESIS;

CYCLIZATION; DIPEPTIDES; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; ESCHERICHIA COLI; HEMOLYSIS; IMIDAZOLIDINES; MAGNETIC RESONANCE SPECTROSCOPY; MICROBIAL SENSITIVITY TESTS; MOLECULAR CONFORMATION; REFERENCE STANDARDS; STEREOISOMERISM;

EID: 53849148291     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200801024     Document Type: Article

References (40)

1. a) M. Iwatsuki, R. Uchida, H. Yoshijima, H. Ui, K. Shiomi, A. Matsumolo, Y. Takahashi, A. Abe, H. Tomoda, S. Omura, J. Antibiot. 2008, 61, 222-229;
2. b) S. Ōmura, H, Tomoda, A. Abe, M. Iwatsuki, Y. Takahashi, PCT WO 2006/304843A1, 2006;
3. c) S. Ōmura, H, Tomoda, A. Abe, M. Iwatsuki, Y. Takahashi, PCT WO 2005/ 090384A1, 2005.
4. R. G. Lingington, M. Robertson, A. Gauthier, B. B. Finlay, R. V. Soest, R. J. Andersen, Org. Lett. 2002, 4, 4089-4092.
5. M. Iwatsuki, R. Uchida, H. Yoshijima, H. Ui, K. Shiomi, Y.-P. Kim, T. Hirose, T. Sunazuka, A. Abe, H. Tomoda, S. Ōmura, J. Antibiot. 2008, 61, 230-236.
6. A. Abe. U. Heczko, R. G. Hegele, B. B. Finlay, J. Exp. Med. 1998, 118, 1907-1916.
7. For a review, see: G. R. Cornelis, F. V. Gijsegem, Annu. Rev. Microbiol. 2000, 54, 735-774.
8. a) For a review, see: C. J. Hueck, Microbiol. Mol. Biol. Rev. 1998, 62, 379-433;
9. b) K. M. Anna, N. Roland, U. Hanna, W. W. Hans, M. Elofsson, Chem. Biol. 2003, 10, 241-249.
10. S. Ōmura, Kekkaku 2000, 75, 599-602.
11. S. Tsuchiya, T. Sunazuka, T. Hirose, R. Mori, T. Tanaka, M. Iwatsuki, S. Ōmura, Org. Lett. 2006, 8, 5577-5580.
12. There are no examples for the stereoselective preparation of 5,6-disubstituted piperazinones, and only two examples of the preparation of a racemate and mixture of diastereomers have been reported, see: a) M. Nyerges, A. Arany, I. Fejes, P. W. Groundwater, W. Zhang, D. Bendell, R. J. Anderson, L. Töke, Tetrahedron 2002, 58, 989-995;
13. b) A. Viso, R. F. de la Pradilla, A. Flores, A. Garcia, M. Tortosa, M. L. López-Rodríguez, J. Org. Chem. 2006, 71, 1142-1148.
14. NOE data are described in the Supporting Information (Figure Sl).
15. a) H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem. 2001, 113, 2056-2075;
16. Angew. Chem. Int. Ed. 2001, 40, 2004-2021;
17. b) Y. Luo, M. A. Blaskovich, G. A. Lajoie, J. Org. Chem. 1999, 6, 1587-1588;
18. c) H. Han, J. Yoon, K. D. Janda, J. Org. Chem. 1998, 63, 2045-2048.
19. O. Cabon, D. Buisson, M. Larcheveque, R. Azerad, Tetrahedron: Asymmetry 1995, 6, 2211-2218.
20. a) A. Abdel-Magid, L. N. Pridegen, D. S. Eggleston, I. Lantos, J. Am. Chem. Soc. 1986, 108, 4595-4602;
21. b) D. A. Evans, J. Bartroli, T. L. Shih, J. Am. Chem. Soc. 1981, 103, 2127-2129.
22. J. Farras, X. Ginesta, P. W. Sutton, J. Taltavull, F. Egelar, P. Romea, F. Urpi, J. Vilarrasa, Tetrahedron 2001, 57, 7665-7674.
23. 1H NMR spectroscopy; see the Supporting Information. (Figures S2 and S3)
24. a) C. Xiong, W. Wang, V. J. Hruby, J. Org. Chem. 2002, 67, 3514-3517;
25. b) Y. G. Gololobov, I. N. Zhmurova, L. F. Kasukhin, Tetrahedron 1981, 37, 437-472.
26. See Figure S4 in the Supporting Information.
27. C. Bonini, L. Chiummiento, M. Pullez, G. Solladié, F. J. Colobert, J. Org. Chem. 2004, 69, 5015-5022.
28. The stereochemistry of the anti-diol unit was checked by NOE observation of compound 38; see the Supporting Information. (Figure S5)
29. 1H NMR spectroscopy.
30. J. A. Marshall, B. G. Shearer, S. L. Crooks, J. Org. Chem. 1987, 52, 1236-1245.
31. S. P. Brown, M. P. Brochu, C. J. Sinz, D. W. C. MacMillan, J. Am. Chem. Soc. 2003, 125, 10808-10809.
32. The stereochemistry of the newly introduced hydroxy group was checked by mean of the modified Mosher's method; see the Supporting Information. (Scheme Sl)
33. a) M. T. Reetz, K. Kesseler, J. Org. Chem. 1985, 50, 5434-5436;
34. b) H. Hagiwara, K. Kimura, H. Uda, J. Chem. Soc. Perkin Trans. 1 1992, 693-700;
35. c) C. Mukai, M. Miyakawa, M. Hanaoka, J. Chem. Soc. Perkin Trans. 1 1997, 913-917.
36. The stereochemistry of the syn-diol unit was checked by NOE observation of a derivative from 42; see the Supporting Information. (Scheme S2)
37. 3).
38. a) Y. Kojima, T. Nakajima, T. Ashizawa, S. Kezuka, T. Ikeno, T. Yamada, Chem. Lett. 2004, 33, 614-615;
39. b) Y. Kojima, T. Nakajima, T. Ikeno, T. Yamada, Synthesis 2004, 12, 1947-1950.
40. B. Drake, M. Patek, M. Lehl, Synthesis 1994, 2, 579-582.