Ring-closing metathesis and photo-fries reaction for the construction of the ansamydn antibiotic kendomycin: Development of a protecting group free oxidative endgame

Chemistry - A European Journal

Volumn 16, Issue 2, 2010, Pages 507-519

  Magauer, Thomas ^a   Martin, Harry J ^a   Mulzer, Johann ^a  

^a UNIVERSITY OF VIENNA   (Austria)

Author keywords

Claisen ireland rearrangement; Metathesis natural products; Polyketides

Indexed keywords

DIASTEREOSELECTIVE; DOUBLE BONDS; FREE END; IRELAND; MACROCYCLES; MACROLACTONIZATION; NATURAL PRODUCTS; PHOTO-FRIES REACTION; POLYKETIDES; PROTECTING GROUP; RING CLOSING METATHESIS; STARTING MATERIALS; TOTAL SYNTHESIS;

GROUP TECHNOLOGY;

SYNTHESIS (CHEMICAL);

ANTIINFECTIVE AGENT; DRUG DERIVATIVE; KENDOMYCIN; RIFABUTIN;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; ECONOMICS; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS;

ANTI-BACTERIAL AGENTS; CYCLIZATION; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; RIFABUTIN; STEREOISOMERISM;

EID: 75649107602     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200902226     Document Type: Article

References (66)

1. a) Y. Funahashi, N. Kawamura, T. Ishimaru, JP Patent 08231551A2960910, 1996 [Chem. Abstr. 1997,126, 6553]:
2. b) Y. Funa-hashi, N. Kawamura, JP Patent 08231552A2960910, 1996 [Chem. Abstr. 1996, 125, 326518];
3. M. H. Su, M. I. Hosken, B. X Holovec, T. L. Johnston, US Patent 5728727A980317, 1998 [Chem. Abstr. 1998, 125,239489].
4. a) H. B. Bode, A. Zeeck. J Chem. Soc. Perkin Trans. 12000. 323;
5. b) H. B. Bode, A. Zeeck, J. Chem. Soc. Perkin Trans. 1 2000, 2665.
6. a) Y. A. Elnakady, M. Rohde, F. Sasse, C. Backes, A. Keller, H.-P. Lenhof, K.J. Weissman, R. Müller, ChemBioChem 2007, 8, 1261;
7. b) C. O. Janssen, S. Lim, E. P. Lo. K. F. Wan, V. C. Yu, M. A. Lee, S. B. Ng, M. X. Everett, A. D. Buss, D. P. Lane, R. S. Boyce, Bioorg. Med. Chem. Lett. 2008,18, 5771.
8. S. C. Wenzel, H. B. Bode. I. Kochems. R. Mueller, ChemBioChem 2008,9,2711.
9. a) M. P. Green, S. Pichlmair, M. M. B. Marques, H. J Martin, O. Diwald, T. Berger, J. Mulzer, Org. Lett. 2004, 6. 3131:
10. b) M. M. B. Marques, S. Pichlmair, H. J. Martin, J. Mulzer, Synthesis 2002, 2766;
11. H. J. Martin, M. Drescher. H. Kählig, S. Schneider. J. Mulzer. Angew. Chem. 2001, 113, 3287;
12. Angew. Chem. Int. Ed. 2001, 40, 3186;
13. Angew. Chem. Int. Ed. 2001, 40, 3186.
14. a) Y. Yu. H. Men. C. Lee, J. Am. Chem. Soc. 2004, 126, 14720;
15. b) A. B. Smith III. E. F. Mesaros. E. Meyer. J. Am. Chem. Soc. 2006, 128, 5292:
16. A. B. Smith III, E. F. Mesaros, E. Meyer, J. Am. Chem. Soc. 2005, 127, 6948;
17. J. T. Lowe. J. S. Panek. Org. Lett. 2008, 10, 3813;
18. e)T. Magauer. H. J. Martin, J. Mulzer. Angew. Chem. 2009, 121, 6148;
19. Angew. Chem. Int. Ed. 2009, 48, 6032.
20. K. B. Bahnck, S.D. Rychnovsky, J. Am. Chem. Soc. 2008, 130, 13177.
21. a) T. Sengoku, D. Uemura. H. Arimoto, Chem. Lett. 2007. 36, 726;
22. b) T. Sengoku, H. Arimoto, D. Uemura, Chem. Commun. 2004, 1220;
23. J. D. White, H. Smits, Org. Lett. 2005. 7, 235;
24. D. Williams, K. Shamim, Org. Lett. 2005. 7. 4161 ;
25. e) J. Mulzer, S. Pichlmair, M. P. Green, M. M. B. Marques, H. J. Martin, Proc. Natl. Acad. Sci. USA 2004, 101, 11980.
26. S. Pichlmair. M. M. B. Marques. M. P. Green. H. J. Martin, J. Mulzer. Org. Lett. 2003,5.4657.
27. J. Uenishi. R. Kawahama. O. J. Yonemitsu, J. Org. Chem. 1997. 62. 1691.
28. E. W. Colvin, B. J. Hamill, J. Chem. Soc. Chem. Commun. 1973, 151.
29. a) E. Negishi, C. Kotora. C. Xu. J. Org. Chem. 1997, 62, 8957:
30. b) Review: E. Negishi, Q. Hu. Z. Huang. M. Qian, G. Wang, Aldri-ehimiea Acta 2005,38,71.
31. W.-H. Jung. C. Harrison, Y. Shin. J. -H. Fournier. R. Balachandran, B. S. Raccor, R. P. Sikorski, A. Vogt, D. P. Curran. B. W. Day, J. Med. Chem. 2007.50.2951.
32. a) M. Scholl. S. Ding, C. W. Lee, R. H. Grubbs, Org. Lett. 1999, 1. 953:
33. b)B. Schwab, R. H. Grubbs, J. W. Ziller. J. Am. Chem. Soc. 1996, 118, 100.
34. At that time we became aware that the White group had unsuccessfully pursued a related approach for the tetrahydropyran formation: H. Smits, PhD Thesis, Oregon State University, 2007.
35. a) R. E. Ireland. D. Habich, D. W. Norbeck. J. Am. Chem. Soc. 1985. 107. 3271;
36. b) R. E. Ireland. P. Wipf, J. D. Armstrong, J. Org. Chem. 1991, 56, 650:
37. R. E. Ireland. R. H. Mueller. A. K. Willard, J. Am. Chem. Soc. 1976. 98. 2868:
38. A. M. M. Castro. Chem. Rev. 2004. 104. 2939.
39. a) K. Mori, Tetrahedron 2008. 64.4060:
40. b) A. G. M. Barrett. R. A. E. Carr, S. V. Attwood, G. Richardson. N. D. A. Walshe. J. Org. Chem. 1986, 51.4840.
41. B. S. Bal, W. E. Childers, H. W. Pinnick. Tetrahedron 1981. 37, 2091.
42. a) Y. Okude, S. Hirano. T. Hiyama, H. Nozaki., J. Am. Chem. Soc. 1976, 98, 3179;
43. b) A. Fürstner, N. Shi, J. Am. Chem. Soc. 1996. 118. 12349;
44. 4 (d.r. 2:1).
45. Claisen-Ireland rearrangements of this dimension are rare in the lit-erature; we are aware of three examples of similar complexity:
46. a) C. E. Stivala, A. Zakarian, J. Am. Chem. Soc. 2008, 130, 3774;
47. b) M. J. Fisher, C. D. Myers, J. Joglar, S. H. Chen, S. J. Danishefsky, J. Org. Chem. 1991, 56, 5826;
48. R. E. Ireland, D. Habich, D. W Nor-beck, J. Am. Chem. Soc. 1985, 107, 3271.
49. a) J. S. Clark, R. Melternich, V.J. Novack, G. S. Sheppard. D. A. Evans, J. Anu Chem. Soc. 1990,112, 866;
50. b) D. A. Evans. J. S. Clark, D. L. Rieger, Tetrahedron 1992, 48, 2127.
51. D. A. Evans, K. T. Chapman, E. M. Carreira, J. Am. Chem. Soc. 1988. 110. 3578.
52. S. Pichlmair, PhD Thesis, University of Vienna. 2004.
53. a) M. R. Winkle. R. C. Ronald, J. Org. Chem. 1982, 47, 2101;
54. b) V. Snieckus, Chem. Rev. 1990, 90, 879.
55. E. Merifield, E. J. Thomas. J. Chem. Soc. Perkin Trans 1 1999, 3269.
56. a) A. Hafner, R. O. Duthaler, R. Marti, G. Rihs, P. Rothe-Streil, F. Schwarzenbach, J. Am. Chem. Soc. 1992, 114, 2321;
57. b) Review: A. Hafner, R. O. Duthaler, Chem. Rev. 1992, 92, 807.
58. a) W. R. Roush, K. Ando, D. B. Powers, A. D. Palkowitz, R. L. Hal-lerman, J. Am. Chem. Soc. 1990, 112, 6339;
59. b) W. R. Roush. R. L. Hallerman, J. Am. Chem. Soc. 1986,108, 294.
60. H. C Brown, S. K. Bhat, J. Am. Chem. Soc. 1986,108, 5919.
61. D. J. Pasto, R. T. Taylor, Organic Reactions, Vol.40 (Ed.: L. A. Pa-quelte), Wiley, New York, 1991, pp. 91-155.
62. 2 with benzene gave a EIZ 2.5:1 mixlure in 80% yield.
63. S. Kulasegaram, R. J. Kulawiec, J Org. Chem. 1997, 62, 6547.
64. E. P. Boden, G. E. Keck. J. Org. Chem. 1985, 50, 2394.
65. Z. Huang, E. Negishi, Org. Lett. 2006, 8, 3675.
66. 2 have been misassigned (com-pare ref. [2;6a-d]).