Total synthesis and complete structural assignment of thiocillin i

Journal of the American Chemical Society

Volumn 133, Issue 15, 2011, Pages 5900-5904

  Aulakh, Virender S ^a,b   Ciufolini, Marco A ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

^b NOVARTIS INSTITUTES FOR BIOMEDICAL RESEARCH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

NATURAL PRODUCTS; STRUCTURAL ASSIGNMENTS; THIOPEPTIDE ANTIBIOTICS; TOTAL SYNTHESIS;

POLYPEPTIDE ANTIBIOTIC AGENT; PYRIDINE DERIVATIVE; THIAZOLE DERIVATIVE; THIOCILLIN I; UNCLASSIFIED DRUG;

ARTICLE; BOHLMANN RAHTZ REACTION; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; DRUG SYNTHESIS; OXIDATION;

ANTI-BACTERIAL AGENTS; MOLECULAR STRUCTURE; PEPTIDES;

EID: 79954535764     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja110166x     Document Type: Article

References (53)

1. Reviews: Bagley, M. C.; Dale, J. W.; Merritt, E. A.; Xiong, X. Chem. Rev. 2005, 105, 685
2. Hughes, R. A.; Moody, C. J. Angew. Chem., Int. Ed. 2007, 46, 7930
3. Arndt, H.-D.; Schoof, S.; Lu, J.-Y. Angew. Chem., Int. Ed. 2009, 48, 6770
4. Shoji, J.; Hinoo, H.; Wakisaka, Y.; Koizumi, K.; Mayama, M.; Matsuura, S.; Matsumoto, K. J. Antibiot. 1976, 24, 366
5. Shoji, J.; Kato, T.; Yoshimura, Y.; Tori, K. J. Antibiot. 1981, 29, 1126
6. Acker, M. G.; Bowers, A. A.; Walsh, C. J. J. Am. Chem. Soc. 2009, 131, 17563
7. Bowers, A. A.; Walsh, C. J.; Acker, M. G. J. Am. Chem. Soc. 2010, 132, 12182
8. Bowers, A. A.; Acker, M. G.; Koglin, A.; Walsh, C. J. J. Am. Chem. Soc. 2010, 132, 7519
9. Walsh, C. J.; Acker, M. G.; Bowers, A. A. J. Biol. Chem. 2010, 286, 27525
10. Wieland Brown, L. C.; Acker, M. G.; Clardy, J.; Walsh, C. T.; Fischbach, M. A. Proc. Natl. Acad. Sci. U.S.A. 2009, 106, 2559
11. Liao, R.; Duan, L.; Lei, C.; Pan, H.; Ding, Y.; Zhang, Q.; Chen, D.; Shen, B.; Yu., Y. Chem. Biol. 2009, 16, 141
12. von Nussbaum, F.; Brands, M.; Hinzen, B.; Weigand, S.; Häbich, D. Angew. Chem., Int. Ed. 2006, 45, 5072
13. Isaacs, D. Indian Pediat. 2005, 42, 9 and references cited therein
14. Hausler, T. Viruses vs Superbugs: A Solution to the Antibiotic Crisis?; Palgrave Macmillan: Houndsmill, U.K., 2006.
15. Nicolaou, K. C.; Nevalainen, M.; Safina, B. S.; Zak, M.; Bulat, S. Angew. Chem., Int. Ed. 2002, 41, 1941
16. Moody, C. J; Hughes, R. A.; Thompson, S. P.; Alcaraz, L. Chem. Commun. 2002, 1760 See also ref 1b.
17. Noteworthy in this regard is the work of Bach: Muller, H. M.; Delgado, O.; Bach, T. Angew. Chem., Int. Ed. 2007, 46, 4771
18. Delgado, O.; Muller, H. M.; Bach, T. Chem.-Eur. J. 2008, 14, 2322 See also: Martin, T.; Laguerre, C.; Hoarau, C.; Marsais, F. Org. Lett. 2009, 11, 3690
19. Martin, T.; Verrier, C.; Hoarau, C.; Marsais, F. Org. Lett. 2008, 10, 2909
20. Ciufolini, M. A.; Shen, Y. C. J. Org. Chem. 1997, 62, 3804
21. Bohlmann, F.; Rahtz, D. Chem. Ber. 1957, 90, 2265 Review: Bagley, M. C.; Glover, C.; Merritt, E. A. Synlett 2007, 2459 Moody introduced the reaction into current synthetic practice during his pioneering synthesis of promothiocin: Moody, C. J.; Bagley, M. C. Chem. Commun. 1998, 2049
22. Bagley, M. C.; Bashford, K. E.; Hesketh, C. L.; Moody, C. J. J. Am. Chem. Soc. 2000, 122, 3301
23. Bagley, M. C.; Dale, J. W.; Bower, J. Chem. Commun. 2002, 1682
24. Bagley, M. C.; Chapaneri, K.; Dale, J. W.; Xiong, X.; Bower, J. J. Org. Chem. 2005, 70, 1389 See also: Bagley, M. C.; Brace, C.; Dale, J. W.; Ohnesorge, M.; Phillips, N. G.; Xiong, X.; Bower, J. J. Chem. Soc., Perkin Trans. 1 2002, 1663
25. Aulakh, V. S.; Ciufolini, M. A. J. Org. Chem. 2009, 74, 5750
26. Synthetic studies: Yonezawa, Y.; Saito, H.; Suzuki, S.; Shin, C.-G. Heterocycles 2002, 57, 903
27. Suzuki, S.; Yonezawa, Y.; Shin, C.-G. Chem. Lett. 2004, 33, 814
28. Review: Ciufolini, M. A.; Lefranc, D. Nat. Prod. Rep. 2010, 27, 330 Total synthesis and full structural elucidation: Lefranc, D.; Ciufolini, M. A. Angew. Chem., Int. Ed. 2009, 48, 4198
29. See refs 8 and, 13 as well as: Ciufolini, M. A.; Shen, Y.-C. Org. Lett. 1999, 1, 1843
30. Merritt, E. A.; Bagley, M. C. Synlett 2007, 954
31. This reaction forms a black precipitate of reduced forms of Se. It is certainly possible that said precipitate entrains byproducts formed during the reaction.
32. The use of IBX for the oxidation of such carbinols was introduced by Moody (ref 9c,9d). We found that the Dess-Martin periodinane performed better than IBX in the oxidation of 14.
33. Bagley, M. C.; Dale, J. W.; Jenkins, R. L.; Bower, J. Chem. Commun. 2004, 102
34. Godet, T.; Bonvin, Y.; Vincent, G.; Ciufolini, M. A. Org. Lett. 2004, 6, 3281
35. Ishihara, K.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 1561
36. Ishihara, K.; Kaneeda, M.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 11179 Review: Yamamoto, H.; Cheon, C. H. In Catalytic Asymmetric Synthesis, 3 rd ed.; Ojima, I., Ed.; John Wiley & Sons: Hoboken, NJ, 2010; Chapter 3, pp 119 ff. Early examples
37. Deaton, M. V.; Ciufolini, M. A. Tetrahedron Lett. 1993, 34, 2409 See also: Ciufolini, M. A.; Zhu, S.; Deaton, M. V. J. Org. Chem. 1997, 62, 7806
38. Bagley, M. C.; Chapaneri, K.; Dale, J. W.; Xiong, X.; Bower, J. J. Org. Chem. 2005, 70, 1389 See also: Bagley, M. C.; Brace, C.; Dale, J. W.; Ohnesorge, M.; Phillips, N. G.; Xiong, X.; Bower, J. J. Chem. Soc., Perkin Trans. 1 2002, 1663
39. Eiden, F.; Herdeis, C. Arch. Pharm. 1977, 310, 744
40. A similar reaction may be carried out in ionic liquids: Karthikeyan, G.; Perumal, P. T. Can. J. Chem. 2005, 83, 1746
41. Nagai, K.; Kamigiri, K.; Arao, N.; Suzumura, K.-I.; Kawano, Y.; Yamaoka, M.; Zhang, H.; Watanabe, M.; Suzuki, K. J. Antibiot. 2003, 56, 123
42. Ref 11 as well as Huang, L.; Quada, J. C., Jr.; Lown, J. W. Het. Commun. 1995, 1, 335
43. Ciufolini, M. A; Valognes, D.; Xi, N. Angew. Chem., Int. Ed. 2000, 39, 2493 and references cited therein
44. Hamada, Y.; Kohda, K.; Shioiri, T. Tetrahedron Lett. 1984, 25, 5303
45. Hamada, Y.; Shibata, M.; Shioiri, T. Tetrahedron Lett. 1985, 26, 5155
46. Hamada, Y.; Shibata, M.; Shioiri, T. Tetrahedron Lett. 1985, 26, 5159
47. Sugiyama, H.; Yokokawa, F.; Shioiri, T. Org. Lett. 2000, 2, 2149
48. For a related construction see ref 12a.
49. 2 is available at modest cost from the Wako Chemical Co., Japan.
50. Nakamura, Y.; Shin, C.-G.; Umemura, K.; Yoshimura, J. Chem. Lett. 1992, 1005
51. Shioiri, T.; Ninomiya, K.; Yamada, S. J. Am. Chem. Soc. 1972, 94, 6203 Use in macrolactamization reactions: Hamada, Y.; Shioiri, T. Chem. Rev. 2005, 105, 4441 Reviews: Shioiri, T. TCIMail 2008, 134, 1 (http://www.tci-asiapacific. com/tcimail/backnumber/article/134drE.pdf)
52. Liang, H. Synlett 2008, 2554
53. 1H NMR spectrum of natural and synthetic thiocillin I (provided as Supporting Information) reveal that all chemical shifts of nonexchangeable protons match to within ±0.01 ppm and coupling constants likewise match. This leaves no doubt that synthetic 1 is structurally identical to authentic thiocilin I.