Total synthesis of phomactin A

Organic Letters

Volumn 11, Issue 7, 2009, Pages 1591-1594

  Tang, Yu ^a   Cole, Kevin P ^a   Buchanan, Grant S ^a   Li, Gang ^a   Hsung, Richard P ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOLOGICAL PRODUCT; FUSED HETEROCYCLIC RINGS; PHOMACTIN A;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

BIOLOGICAL PRODUCTS; CRYSTALLOGRAPHY, X-RAY; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 64349103353     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol900237e     Document Type: Article

References (80)

1. Sugano, M.; Sato, A.; Iijima, Y.; Oshima, T.; Furuya, K.; Kuwano, H.; Hata, T.; Hanzawa, H. J. Am. Chem. Soc. 1991, 113, 5463.
2. (a) Sugano, M.; Sato, A.; Saito, K.; Takaishi, S.; Matsushita, Y.; Iijima, Y. J. Med. Chem. 1996, 39, 5281.
3. (b) Sugano, M.; Sato, A.; Iijima, Y.; Furuya, K.; Hata, T.; Kuwano, H. J. Antibiot. 1995, 48, 1188.
4. (c) Sugano, M.; Sato, A.; Iijima, Y.; Furuya, K.; Haruyama, H.; Yoda, K.; Hata, T. J. Org. Chem. 1994, 59, 564.
5. Koyama, K.; Ishino, K.; Takatori, K.; Takashi Sugita, T.; Kinoshita, K.; Takahashi, K. Tetrahedron Lett. 2004, 45, 6947.
6. Also see: Zhu, X.; Lambertino, A. T.; Houghton, T. J.; McGilvra, J. D.; Xu, C; Rawal, V. H.; Leff, A. R. Life Sci. 2003, 73, 3005.
7. For reviews on synthetic efforts toward phomactins, see: (a) Cole, K. P.; Hsung, R. P. ChemTracts 2003, 16, 811.
8. (b) Goldring, W. P. D.; Pattenden, G. Acc. Chem. Res. 2006, 39, 354.
9. For synthetic approaches, see: (a) Foote, K. M.; Hayes, C. J.; Pattenden, G. Tetrahedron Lett. 1996, 37, 275.
10. (b) Chen, D.; Wang, J.; Totah, N. I. J. Org. Chem. 1999, 64, 1776.
11. (c) Seth, P. P.; Totah, N. I. J. Org. Chem. 1999, 64, 8750.
12. (d) Seth, P. P.; Totah, N. I. Org. Lett. 2000, 2, 2507.
13. (e) Kallan, N. C; Halcomb, R. L. Org. Lett. 2000, 2, 2687.
14. (f) Chemler, S. R.; Danishefsky, S. J. Org. Lett. 2000, 2, 2695.
15. (g) Seth, P. P.; Chen, D.; Wang, J.; Gao, X.; Totah, N. I. Org. Lett. 2000, 56, 10185.
16. (h) Foote, K.; John, M.; Pattenden, G. Synlett., 2001, 365.
17. (i) Mi, B.; Maleczka, R. Org. Lett. 2001, 3, 1491.
18. (j) Chemler, S. R.; Iserloh, U.; Danishefsky, S. J. Org. Lett. 2001, 3, 2949.
19. (k) Houghton, T.; Choi, S.; Rawal, V. H. Org. Lett. 2001, 3, 3615.
20. (l) Mohr, P. J.; Halcomb, R. L. Org. Lett. 2002, 4, 2413.
21. (m) Balnaves, A. S.; McGowan, G.; Shapland, P. D. P.; Thomas, E. J. Tetrahedron Lett. 2003, 44, 2713.
22. (n) Cheing, J. W. C; Goldring, W. P. D.; Pattenden, G. Chem. Commun. 2003, 2788.
23. (o) Ryu, K.; Cho, Y.-S.; Jung, S.-I.; Cho, C.-G. Org. Lett. 2006, 8, 3343.
24. (p) Huang, J.; Wang, H; Wu, C; Wulff, W. D. Org. Lett. 2007, 9, 2799.
25. (q) Seth, P. P.; Chen, D.; Wang, J.; Gao, X.; Totah, N. I. Tetrahedron Lett. 2007, 48, 4605.
26. (r) Peng, W.; Lee, C.-S. Synlett., 2008, 142.
27. (s) DiBlasi, C. M.; Hamblett, C. L.; Leighton, J. L. Abstracts of Papers, 224th National Meeting of the American Chemical Society, Boston, MA, Fall, 2002; American Chemical Society: Washington, DC, 2002; ORGN-364.
28. Platelet-activating factor is a phospholipid mediator released in the body by several cell types that play a role in causing inflammatory diseases. See: (a) Koltai, M.; Braquet, P. G. Clin. Rev. Allergy 1994, 12, 361.
29. (b) Xhu, X.; Muñoz, N. M.; Kim, K. P.; Sano, H.; Cho, W.; Leff, A. R. J. Immunol. 1999, 163, 3423.
30. For a total synthesis of (+) -phomactin D, see: Myaoka, H.; Saka, Y.; Mura, S.; Yamada, Y. Tetrahedron Lett. 1996, 37, 7107.
31. For a total synthesis of (±) -phomactin A, see: (a) Goldring, W. P. D.; Pattenden, G. Chem. Commun. 2002, 1736.
32. (b) Diaper, C. M.; Goldring, W. P. D.; Pattenden, G. Org. Biomol. Chem. 2003, 1, 3949.
33. (c) Foote, K. M.; Hayes, C. J.; John, M. P.; Pattenden, G. Org. Biomol. Chem.2003, 1, 3917.
34. For a total synthesis of (+) -phomactin A, see: Mohr, P. J.; Halcomb, R. L. J. Am. Chem. Soc. 2003, 125, 1712.
35. For a total synthesis of (±) -phomactin B2, see: Huang, J.; Wu, C.; Wulff, W. D. J. Am. Chem. Soc. 2007, 129, 13366.
36. Cole, K. P.; Hsung, R. P. Org. Lett. 2003, 5, 4843.
37. For reviews, see: (a) Harrity, J. P. A.; Provoost, O. Org. Biomol. Chem. 2005, 3, 1349.
38. (b) Hsung, R. P.; Kurdyumov, A. V.; Sydorenko, N. Eur. J. Org. Chem. 2005, 1, 23.
39. (c) Hsung, R. P.; Cole, K. P. In Strategies and Tactics in Organic Synthesis; Harmata, M., Ed.; Elsevier Science, Pergamon Press: Oxford, UK, 2004; Vol. 4, p 41.
40. For our work, see: (a) Kurdyumov, A. V.; Lin, N.; Hsung, R. P.; Gullickson, G. C.; Cole, K. P.; Sydorenko, N.; Swidorski, J. J. Org. Lett. 2006, 8, 191.
41. (b) Shen, H. C.; Wang, J.; Cole, K. P.; McLaughlin, M. J.; Morgan, C. D.; Douglas, C. J.; Hsung, R. P.; Coverdale, H. A.; Gerasyuto, A. I.; Hahn, J. M.; Liu, J.; Wei, L.-L.; Sklenicka, H. M.; Zehnder, L. R.; Zificsak, C. A. J. Org. Chem. 2003, 68, 1729.
42. (c) Hsung, R. P.; Wei, L.-L.; Sklenicka, H. M.; Douglas, C. J.; McLaughlin, M. J.; Mulder, J. A.; Yao, L. Org. Lett. 1999, 1, 509.
43. (d) Hsung, R. P.; Shen, H. C.; Douglas, C. J.; Morgan, C. D.; Degen, S. J.; Yao, L. J. J. Org. Chem. 1999, 64, 690.
44. For recent related studies, see: (a) Brioche, J. C. R.; Goodenough, K. M.; Whatrup, D. J.; Harrity, J. P. A. J. Org. Chem. 2008, 73, 1946.
45. (b) Yavari, I.; Sabbaghan, M.; Hossaini, Z. Synlett 2008, 1153.
46. (c) Hubert, C.; Moreau, J.; Batany, J.; Duboc, A.; Hurvois, J.-P.; Renaudb, J.-L. Adv. Syn. Cat. 2008, 350, 40.
47. (d) Zhu, M.; Wei, Q.; Gong, L. Adv. Synth. Catal. 2008, 350, 1281.
48. (e) Zhong, W.; Lin, F.; Chen, R.; Su, W. Synthesis 2008, 2561.
49. (f) Brioche, J. C. R.; Goodenough, K. M.; Whatrup, D. J.; Harrity, J. P. A. Org. Lett. 2007, 9, 3491.
50. (g) Lee, Y. R.; Xia, L. Synthesis 2007, 3240.
51. (h) Epstein, O. L.; Rovis, T. J. Am. Chem. Soc. 2006, 128, 16480.
52. For applications in natural product syntheses, see: (a) Kurdyumov, A. V.; Hsung, R. P. J. Am. Chem. Soc. 2006, 128, 6272.
53. (b) Kurdyumov, A. V.; Hsung, R. P.; Ihlen, K.; Wang, J. Org. Lett. 2003, 5, 3935.
54. (c) Hsung, R. P.; Cole, K. P.; Zehnder, L. R.; Wang, J.; Wei, L.-L.; Yang, X.-F.; Coverdale, H. A. Tetrahedron 2003, 59, 311.
55. (d) Zehnder, L. R.; Hsung, R. P.; Wang, J.; Golding, G. M. Angew. Chem., Int. Ed. 2000, 39, 3876.
56. (e) Malerich, J. P.; Trauner, D. J. Am. Chem. Soc. 2003, 125, 9554.
57. (f) Olson, B. S.; Trauner, D. Synlett., 2005, 700.
58. (g) Sunazuka, T.; Handa, M.; Nagai, K.; Shirahata, T.; Harigaya, Y.; Otoguro, K.; Kuwajima, I.; Õmura, S. Tetrahedron 2004, 60, 7845.
59. Hu, H.; Harrison, T. J.; Wilson, P. D. J. Org. Chem. 2004, 69, 3782.
60. (h) Lee, Y. R.; Wang, X. Bull. Korean Chem. Soc. 2005, 26, 1933.
61. Cole, K. P.; Hsung, R. P. Chem. Commun. 2005, 5784.
62. You, L.; Hsung, R. P.; Bedermann, A. A.; Kurdyumov, A. K.; Tang, Y.; Buchanan, G. S.; Cole, K. P. Adv. Syn. Catal. 2008, 350, 2885.
63. (a) Kozmin, S. A.; Rawal, V. H. J. Org. Chem. 1997, 62, 5252.
64. (b) Kozmin, S. A.; Rawal, V. H. J. Am. Chem. Soc. 1999, 121, 9562.
65. (a) Kozmin, S. A.; Green, M. T.; Rawal, V. H. J. Org. Chem.1999, 64, 8045.
66. (b) Huang, Y.; Iwama, T.; Rawal, V. H. J. Am. Chem. Soc. 2000, 122, 7843.
67. (c) Huang, Y.; Iwama, T.; Rawal, V. H. Org. Lett. 2002, 4, 1163.
68. (d) Kozmin, S. A.; Iwama, T.; Huang, Y.; Rawal, V. H. J. AM. Chem. Soc. 2002, 124, 4628.
69. See the Supporting Information.
70. Spartan models of enone 15 and epoxy ketone 16 reveal conformations similar to that of endo-peroxide 8.
71. For related protocols, see: (a) Boyer, F.-D.; Hanna, I. J. Org. Chem. 2005, 70, 1077.
72. (b) Iranpoor, N.; Shekarriz, M.; Shiriny, F. Synth. Commun. 1998, 28, 347.
73. Dauben, W. G.; Michno, D. M. J. Org. Chem. 1977, 42, 682.
74. For a recent example, see: (a) Chai, Y.; McIntosh, M. C. Tetrahedron. 2004, 45, 3269. Also see:
75. (b) Sundararaman, P.; Herz, W. J. Org. Chem. 1977, 42, 813.
76. (c) Chu, A.; Mander, L. N. Tetrahedron Lett. 1988, 29, 2727.
77. 3 that was successful in a related 1, 3-transposition; see: (a) John, M.; Hutchison, J. M.; Lindsay, H. A.; Dormi, S. S.; Jones, G. D.; Vicic, D. A.; McIntosh, M. C. Org. Lett. 2006, 8, 3663. Also see:
78. (b) Jacob, J.; Espenson, J. H.; Jensen, J. H.; Gordon, M. S. Organomet al.lics 1998, 17, 1835.
79. (c) Morrill, C.; Grubbs, R. H. J. Am. Chem. Soc. 2005, 127, 2842.
80. Wydra, H.; Paryzek, Z. Tetrahedron. 1984, 25, 2601.