Total synthesis of (+)-pleuromutilin

Chemistry - A European Journal

Volumn 19, Issue 21, 2013, Pages 6718-6723

  Fazakerley, Neal J ^a   Helm, Matthew D ^a   Procter, David J ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

natural products; pleuromutilin; radicals; samarium; total synthesis

Indexed keywords

ELECTRON TRANSFER REDUCTIONS; ENANTIOSPECIFIC; NATURAL PRODUCTS; PLEUROMUTILIN; RADICALS; TOTAL SYNTHESIS;

CYCLIZATION; FREE RADICAL REACTIONS; SAMARIUM;

SYNTHESIS (CHEMICAL);

ANTIINFECTIVE AGENT; BIOLOGICAL PRODUCT; DIHYDROCARVONE; DITERPENE; KETONE; MUTILIN; PLEUROMUTILIN; POLYCYCLIC HYDROCARBON; TERPENE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

ANTI-BACTERIAL AGENTS; BIOLOGICAL PRODUCTS; CYCLIZATION; DITERPENES; KETONES; MOLECULAR STRUCTURE; MONOTERPENES; POLYCYCLIC COMPOUNDS; STEREOISOMERISM;

EID: 84877786236     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201300968     Document Type: Article

References (77)

1. F. Kavanagh, A. Hervey, W. J. Robbins, Proc. Natl. Acad. Sci. USA 1951, 37, 570
2. F. Kavanagh, A. Hervey, W. J. Robbins, Proc. Natl. Acad. Sci. USA 1952, 38, 555.
3. G. Hogenauer, Eur. J. Biochem. 1975, 52, 93.
4. Y. Z. Tang, Y. H. Liu, J. X. Chen, Mini-Rev. Med. Chem. 2012, 12, 53
5. H. A. Kirst, Expert Opin. Ther. Pat. 2012, 22, 15
6. D. N. Wilson, Ann. N.Y. Acad. Sci. 2011, 1241, 1
7. R. Novak, Ann. N.Y. Acad. Sci. 2011, 1241, 71.
8. E. G. Gibbons, J. Org. Chem. 1980, 45, 1540
9. E. G. Gibbons, J. Am. Chem. Soc. 1982, 104, 1767
10. E. G. Gibbons, PhD Thesis, Harvard University, 1982.
11. R. K. Boeckman, Jr., D. M. Springer, T. R. Alessi, J. Am. Chem. Soc. 1989, 111, 8284
12. D. M. Springer, PhD Thesis, The University of Rochester, 1989.
13. E. Bacqué, F. Pautrat, S. Z. Zard, Chem. Commun. 2002, 2312
14. E. Bacqué, F. Pautrat, S. Z. Zard, Org. Lett. 2003, 5, 325.
15. J. Liu, S. D. Lotesta, E. J. Sorensen, Chem. Commun. 2011, 47, 1500
16. S. D. Lotesta, J. Liu, E. V. Yates, L. Krieger, J. C. Sacchettini, J. S. Freundlich, E. J. Sorensen, Chem. Sci. 2011, 2, 1258.
17. 2, see
18. H. Y. Harb, D. J. Procter, Synlett 2012, 6
19. M. Szostak, D. J. Procter, Angew. Chem. 2012, 124, 9372
20. Angew. Chem. Int. Ed. 2012, 51, 9238
21. M. Szostak, M. Spain, D. Parmar, D. J. Procter, Chem. Commun. 2012, 48, 330
22. M. Szostak, D. J. Procter, Angew. Chem. 2011, 123, 7881
23. Angew. Chem. Int. Ed. 2011, 50, 7737
24. D. J. Procter, R. A. Flowers II, T. Skrydstrup, Organic Synthesis using Samarium Diiodide: A Practical Guide, RSC, Cambridge, 2010
25. K. C. Nicolaou, S. P. Ellery, J. S. Chen, Angew. Chem. 2009, 121, 7276
26. Angew. Chem. Int. Ed. 2009, 48, 7140
27. R. A. Flowers II, Synlett 2008, 1427
28. K. Gopalaiah, H. B. Kagan, New J. Chem. 2008, 32, 607
29. D. J. Edmonds, D. Johnston, D. J. Procter, Chem. Rev. 2004, 104, 3371
30. A. Dahlén, G. Hilmersson, Eur. J. Inorg. Chem. 2004, 3393
31. H. B. Kagan, Tetrahedron 2003, 59, 10351.
32. M. D. Helm, D. Sucunza, M. Da Silva, M. Helliwell, D. J. Procter, Tetrahedron Lett. 2009, 50, 3224
33. M. D. Helm, M. Da Silva, D. Sucunza, M. Helliwell, D. J. Procter, Tetrahedron 2009, 65, 10816. For background studies, see
34. T. J. K. Findley, D. Sucunza, L. C. Miller, D. T. Davies, D. J. Procter, Chem. Eur. J. 2008, 14, 6862
35. 2-mediated dialdehyde cyclisation cascade, see
36. J. Y. Cha, J. T. S. Yeoman, S. E. Reisman, J. Am. Chem. Soc. 2011, 133, 14964.
37. M. D. Helm, M. Da Silva, D. Sucunza, T. J. K. Findley, D. J. Procter, Angew. Chem. 2009, 121, 9479
38. Angew. Chem. Int. Ed. 2009, 48, 9315.
39. J. D. White, U. M. Grether, C. S. Lee, Org. Synth. 2005, 82, 108
40. S. L. Schreiber, J. Am. Chem. Soc. 1980, 102, 6163
41. G. Solladie, J. Hutt, J. Org. Chem. 1987, 52, 3560.
42. R. C. Larock, T. R. Hightower, Tetrahedron Lett. 1995, 36, 2423
43. Y. Ito, T. Hirao, T. Saegusa, J. Org. Chem. 1978, 43, 1011.
44. B. M. Trost, D. M. T. Chan, J. Am. Chem. Soc. 1982, 104, 3733
45. A. Hosomi, Y. Sakata, H. Sakurai, Carbohydr. Res. 1987, 171, 223.
46. D. L. Comins, A. Dehghani, Tetrahedron Lett. 1992, 33, 6299.
47. W. H. Pearson, J. E. Kropf, A. L. Choy, I. Y. Lee, J. W. Kampf, J. Org. Chem. 2007, 72, 4135.
48. A. Hosomi, H. Sakurai, Tetrahedron Lett. 1976, 17, 1295
49. A. Hosomi, M. Endo, H. Sakurai, Chem. Lett. 1976, 941.
50. D. B. Dess, J. C. Martin, J. Org. Chem. 1983, 48, 4155.
51. A. L. J. Beckwith, Tetrahedron 1981, 37, 3073.
52. III enolates, see:, I. M. Rudkin, L. C. Miller, D. J. Procter, Organomet. Chem. 2008, 34, 19.
53. For an illustration of the importance of pre-coordination, see:, D. Johnston, E. Couché, D. J. Edmonds, K. W. Muir, D. J. Procter, Org. Biomol. Chem. 2003, 1, 328.
54. 2, see:, D. P. Curran, T. L. Fevig, C. P. Jasperse, M. J. Totleben, Synlett 1992, 943.
55. CCDC-913369 (19) 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.
56. M. Szostak, M. Spain, D. J. Procter, Chem. Commun. 2011, 47, 10254
57. M. Szostak, M. Spain, D. J. Procter, Org. Lett. 2012, 14, 840
58. M. Szostak, K. D. Collins, N. J. Fazakerley, M. Spain, D. J. Procter, Org. Biomol. Chem. 2012, 10, 5820.
59. B. S. Bodnar, P. F. Vogt, J. Org. Chem. 2009, 74, 2598.
60. D. H. R. Barton, S. J. McCombie, J. Chem. Soc. Perkin Trans. 1 1975, 1574. For the removal of tin residues, see
61. D. C. Harrowven, D. P. Curran, S. L. Kostiuk, I. L. Wallis-Guy, S. Whiting, K. J. Stenning, B. Tang, E. Packard, L. Nanson, Chem. Commun. 2010, 46, 6335.
62. K. S. Kim, Y. H. Song, B. H. Lee, C. S. Hahn, J. Org. Chem. 1986, 51, 404
63. D. A. Evans, H. P. Ng, D. L. Rieger, J. Am. Chem. Soc. 1993, 115, 11446.
64. D. V. Patel, R. J. Schmidt, E. M. Gordon, J. Org. Chem. 1992, 57, 7143
65. R. H. Wollenberg, K. F. Albizati, R. Peries, J. Am. Chem. Soc. 1977, 99, 7365
66. A. J. Leusink, H. A. Budding, J. W. Marsman, J. Organomet. Chem. 1967, 9, 285.
67. B. Zeynizadeh, T. Behyar, Bull. Chem. Soc. Jpn. 2005, 78, 307.
68. E. J. Corey, C. U. Kim, M. Takeda, Tetrahedron Lett. 1972, 13, 4339.
69. A. Hirai, A. Matsui, K. Komatsu, K. Tanino, M. Miyashita, Chem. Commun. 2002, 1970
70. T. Carrillo-Marquez, L. Caggiano, R. F. W. Jackson, U. Grabowska, A. Rae, M. J. Tozer, Org. Biomol. Chem. 2005, 3, 4117
71. R. K. Dieter, F. Guo, Org. Lett. 2008, 10, 2087
72. F. Yoshimura, A. Matsui, A. Hirai, K. Tanino, M. Miyashita, Tetrahedron Lett. 2009, 50, 5126.
73. M. Arai, T. Kawasuji, E. Nakamura, J. Org. Chem. 1993, 58, 5121.
74. J. D. Hinks, A. K. Takle, E. Hunt, PCT Int. Appl. 1997, WO 9725309A1 19970717
75. D. K. Dean, S. Howard, A. Naylor, A. K. Takle, PCT Int. Appl. 2000, WO 2000073287A1 20001207
76. J. Yang, PCT Int. Appl. 2007, WO 2007062334A2 20070531
77. A. M. Diederich, J. Sisko, F. G. Vogt, PCT Int. Appl. 2007, WO 2007062335A2 20070531.