Access to the aeruginosin serine protease inhibitors through the nucleophilic opening of an oxabicyclo[2.2.1]heptane: Total synthesis of microcin SF608

Chemistry - A European Journal

Volumn 20, Issue 20, 2014, Pages 6071-6080

  Diethelm, Stefan ^a   Schindler, Corinna S ^a   Carreira, Erick M ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

aeruginosins; epoxide reduction; hydroindoles; natural products; serine protease inhibitors

Indexed keywords

AMINO ACIDS; ATOMS; DISEASES; HEPTANE; HYDROGEN; SYNTHESIS (CHEMICAL);

AERUGINOSINS; EPOXIDE REDUCTION; HYDROINDOLES; NATURAL PRODUCTS; SERINE PROTEASE INHIBITOR;

REGIOSELECTIVITY;

EID: 84900034143     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201400046     Document Type: Article

References (59)

1. M. A. Phillips, R. J. Fletterick, Curr. Biol. Curr. Opin. Sturct. Biol. 1992, 2, 713-720.
2. Proteases in Health and Disease in Progress in Molecular Biology and Translational Science Vol. 99 (Ed:, E. Di Cerca,), Elsevier Academic Press, Burlington, 2011, pp. 1-313.
3. D. Voet, J. G. Voet, in Biochemistry 4th edition, John Wiley & Sons, Hoboken, 2011, 525-538; on the mechanism of serine proteases, see also
4. C. S. Craik, S. Roczniak, C. Largman, W. R. Rutter, Science 1987, 237, 909-913.
5. M. Murakami, Y. Okita, H. Matsuda, T. Okino, K. Yamaguchi, Tetrahedron Lett. 1994, 35, 3129-3132.
6. K. Ersmark, J. R. Del Valle, S. Hanessian, Angew. Chem. 2008, 120, 1220-1242
7. Angew. Chem. Int. Ed. 2008, 47, 1202-1223
8. for the isolation of microcin SF608, see:, R. Banker, S. Carmeli, Tetrahedron 1999, 55, 10835-10844
9. for the isolation of dysinosin A, see:, A. R. Carroll, G. K. Pierens, G. Fechner, P. deAlmeida Leone, A. Ngo, M. Simpson, E. Hyde, J. N. A. Hooper, S.-L. Boström, D. Musil, R. J. Quinn, J. Am. Chem. Soc. 2002, 124, 13340-13341.
10. The guanidine group has been shown to play a key role in binding of the aeruginosin to the active site of serine proteases. For crystal structures of serine proteases in complex with aeruginosin peptides, see ref. [5a] and in particular:, J. L. Rios Steiner, M. Murakami, A. Tulinsky, J. Am. Chem. Soc. 1998, 120, 597-598.
11. A. Pluotno, S. Carmeli, Tetrahedron 2005, 61, 575-583
12. for the isolation of related natural products, see:, K. Fujii, K. Sivonen, K. Adachi, K. Noguchi, Y. Shimizu, H. Sano, K. Hirayama, M. Suzuki, K. Harada, Tetrahedron Lett. 1997, 38, 5529-5532.
13. N. Valls, M. Lõpez-Canet, M. Vallribera, J. Bonjoch, J. Am. Chem. Soc. 2000, 122, 11248-11249
14. P. Wipf, J.-L. Methot, Org. Lett. 2000, 2, 4213-4216
15. Y. Fukuta, T. Ohshima, V. Gnanadesikan, T. Shibuguchi, T. Nemoto, T. Kisugi, T. Okino, M. Shibasaki, Proc. Natl. Acad. Sci. USA 2004, 101, 5433-5438
16. S. Hanessian, R. Margarita, A. Hall, S. Johnstone, M. Tremblay, L. Parlanti, J. Am. Chem. Soc. 2002, 124, 13342-13343
17. S. Hanessian, M. Tremblay, J. F. W. Petersen, J. Am. Chem. Soc. 2004, 126, 6064-6071.
18. C. S. Schindler, C. R. J. Stephenson, E. M. Carreira, Angew. Chem. 2008, 120, 8984-8987
19. Angew. Chem. Int. Ed. 2008, 47, 8852-8855.
20. C. S. Schindler, L. Bertschi, E. M. Carreira, Angew. Chem. Int. Ed. 2010, 49, 9229-9232.
21. C. S. Schindler, S. Diethelm, E. M. Carreira, Angew. Chem. 2009, 121, 6414-6417
22. Angew. Chem. Int. Ed. 2009, 48, 6296-6299.
23. For a previous total synthesis of microcin SF608, see:, N. Valls, M. Vallribera, M. Lõpez-Canet, J. Bonjoch, J. Org. Chem. 2002, 67, 4945-4950.
24. S. Diethelm, C. S. Schindler, E. M. Carreira, Org. Lett. 2010, 12, 3950-3953.
25. NHC ligand 15 was synthesized according to:, A. J. Arduengo III, R. Krafczyk, R. Schmutzler, H. A. Craig, J. R. Goerlich, W. J. Marshall, M. Unverzagt, Tetrahedron 1999, 55, 14523-14534.
26. V. Jurkauskas, J. P. Sadighi, S. L. Buchwald, Org. Lett. 2003, 5, 2417-2420.
27. D. A. Evans, T. C. Britton, J. A. Ellman, R. L. Dorow, J. Am. Chem. Soc. 1990, 112, 4011-4030.
28. P. Magnus, A. H. Payne, M. J. Waring, D. A. Scott, V. Lynch, Tetrahedron Lett. 2000, 41, 9725-9730.
29. A. G. Myers, B. Zheng, Tetrahedron Lett. 1996, 37, 4841-4844.
30. CCDC-785240 (26) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
31. S. Murai, T. Murai, S. Kato, in Comprehensive Organic Synthesis Vol. 8 (Eds. , B. M. Trost, I. Fleming,), Pergamon, Oxford, 1991, pp. 871-893.
32. T. V. RajanBabu, W. A. Nugent, M. S. Beattie, J. Am. Chem. Soc. 1990, 112, 6408-6409
33. T. V. RajanBabu, W. A. Nugent, J. Am. Chem. Soc. 1994, 116, 986-997
34. for a review on titanium mediated epoxide reduction, see:, A. Gansäuer, T. Lauterbach, S. Narayan, Angew. Chem. 2003, 115, 5714-5731
35. Angew. Chem. Int. Ed. 2003, 42, 5556-5573.
36. K. Daasbjerg, H. Svith, S. Grimme, M. Gerenkamp, C. Mück- Lichtenfeld, A. Gansäuer, A. Barchuk, F. Keller, Angew. Chem. 2006, 118, 2095-2098
37. Angew. Chem. Int. Ed. 2006, 45, 2041-2044
38. A. Gansäuer, A. Barchuk, F. Keller, M. Schmitt, S. Grimme, M. Gerenkamp, C. Mück-Lichtenfeld, K. Daasbjerg, H. Svith, J. Am. Chem. Soc. 2007, 129, 1359-1371.
39. D. A. Spiegel, K. B. Wiberg, L. N. Schacherer, M. R. Medeiros, J. L. Wood, J. Am. Chem. Soc. 2005, 127, 12513-12515
40. J. Jin, M. Newcomb, J. Org. Chem. 2007, 72, 5098-5103; for a related example, see
41. D. Pozzi, E. M. Scanlan, P. Renaud, J. Am. Chem. Soc. 2005, 127, 14204-14205; for computational studies, see
42. W. Tantaway, H. Zipse, Eur. J. Org. Chem. 2007, 5817-5820.
43. J. M. Cuerva, A. G. Campaña, J. Justicia, A. Rosales, J. L. Oller-Lõpez, R. Robles, D. J. Cárdenas, E. Buñuel, J. E. Oltra, Angew. Chem. 2006, 118, 5648-5652
44. Angew. Chem. Int. Ed. 2006, 45, 5522-5526
45. J. Jin, M. Newcomb, J. Org. Chem. 2008, 73, 7901-7905
46. M. Paradas, A. G. Campaña, T. Jiménez, R. Robles, J. E. Oltra, E. Buñuel, J. Justicia, D. J. Cárdenas, J. M. Cuerva, J. Am. Chem. Soc. 2010, 132, 12748-12756.
47. B. F. Yates, L. Radom, J. Am. Chem. Soc. 1987, 109, 2910-2915
48. V. Vrček, H. Zipse, J. Org. Chem. 2009, 74, 2947-2957.
49. C. K. Lau, C. Dufresne, P. C. Bélanger, S. Piétré, J. Scheigetz, J. Org. Chem. 1986, 51, 3038-3043.
50. For a review covering radical deoxygenation of alcohols, see:, W. Hartwig, Tetrahedron 1983, 39, 2609-2645.
51. I. Saito, H. Ikehira, R. Kasatani, M. Watanabe, T. Matsuura, J. Am. Chem. Soc. 1986, 108, 3115-3117; for an application of this methodology in the context of natural product synthesis, see also
52. A. G. Myers, K. R. Condroski, J. Am. Chem. Soc. 1995, 117, 3057-3083.
53. R. F. Newton, D. P. Reynolds, M. A. W. Finch, D. R. Kelly, S. M. Roberts, Tetrahedron Lett. 1979, 20, 3981-3982
54. A. S. Pilcher, D. K. Hill, S. J. Shimshock, R. E. Waltermire, P. DeShong, J. Org. Chem. 1992, 57, 2492-2495.
55. J. Coste, D. Le-Nguyen, B. Castro, Tetrahedron Lett. 1990, 31, 205-208.
56. H. Li, X. Jiang, Y.-h. Ye, C. Fan, T. Romoff, M. Goodman, Org. Lett. 1999, 1, 91-93.
57. For a review covering peptide coupling reagents, see:, E. Valeur, M. Bradley, Chem. Soc. Rev. 2009, 38, 606-631.
58. K. Feichtinger, C. Zapf, H. L. Sings, M. Goodman, J. Org. Chem. 1998, 63, 3804-3805
59. K. Feichtinger, H. L. Sings, T. Baker, K. Matthews, M. Goodman, J. Org. Chem. 1998, 63, 8432-8439.