Enantioselective total synthesis of (+)-stachyflin: A potential anti-influenza a virus agent isolated from a microorganism

European Journal of Organic Chemistry

Volumn , Issue 16, 2011, Pages 2948-2957

  Sakurai, Junji ^a   Kikuchi, Takuya ^a   Takahashi, Ohgi ^a   Watanabe, Kazuhiro ^a   Katoh, Tadashi ^a  

^a TOHOKU PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

Antiviral agents; Hemagglutinin inhibitor; Influenza A; Natural products; Stachyflin; Total synthesis

Indexed keywords

EID: 79956339780     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201100173     Document Type: Article

References (42)

1. G. Neumann, T. Noda, Y. Kawaoka, Nature 2009, 459, 931-939.
2. J. Cohen, M. Enserink, Science 2009, 324, 1496-1497.
3. P. E. Aldrich, E. C. Hermann, W. E. Meier, M. Paulshock, W. W. Prichard, J. A. Snyder, J. C. Watts, J. Med. Chem. 1971, 14, 535-543.
4. E. De Clercq, Nat. Rev. Drug Discovery 2006, 5, 1015-1025.
5. M. Schmidtke, R. Zell, K. Bauer, A. Krumbholtz, C. Schrader, J. Suess, P. Wutzler, Intervirology 2006, 49, 286-293.
6. A. Moscona, N. Engl. J. Med. 2009, 360, 953-956.
7. T. Kamigauchi, T. Fujiwara, H. Tani, Y. Kawamura, I. Horibe (Shionogi & Co., Ltd., Japan), PCT WO 9711947 A1, 03 April, 1997.
8. K. Minagawa, S. Kouzuki, J. Yoshimoto, Y. Kawamura, H. Tani, T. Iwata, Y. Terui, H. Nakai, S. Yagi, N. Hattori, T. Fujiwara, T. Kamigauchi, J. Antibiot. 2002, 55, 155-164.
9. K. Minagawa, S. Kouzuki, T. Kamigauchi, J. Antibiot. 2002, 55, 165-171.
10. J. Yoshimoto, S. Yagi, J. Ono, K. Sugita, N. Hattori, T. Fujioka, T. Fujiwara, H. Sugimoto, N. Hashimoto, J. Pharm. Pharmacol. 2000, 52, 1247-1255.
11. S. Yagi, J. Ono, J. Yoshimoto, K. Sugita, N. Hattori, T. Fujioka, T. Fujiwara, H. Sugimoto, K. Hirano, N. Hashimoto, Pharm. Res. 1999, 16, 1041-1046.
12. J. Yoshimoto, M. Kakui, H. Iwasaki, H. Sugimoto, T. Fujiwara, N. Hattori, Microbiol. Immunol. 2000, 44, 677-685.
13. J. Yoshimoto, M. Kakui, H. Iwasaki, T. Fujiwara, H. Sugimoto, N. Hattori, Arch. Virol. 1999, 144, 865-878.
14. R. G. Douglas Jr., N. Eng. J. Med. 1990, 322, 443-450.
15. S. M. Wintermeyer, M. C. Nahata, Ann. Pharmacother. 1995, 29, 299-310.
16. M. von Itzstein, W. Y. Wu, G. B. Kok, M. S. Pegg, J. C. Dyason, B. Jin, T. Van Phan, M. L. Smythe, H. F. White, S. W. Oliver, P. M. Colman, J. N. Varghese, D. M. Ryan, J. M. Woods, R. C. Bethell, V. J. Hotham, J. M. Cameron, C. R. Penn, Nature 1993, 363, 418-423.
17. C. U. Kim, W. Lew, M. A. Williams, H. Liu, L. Zhang, S. Swaminathan, N. Bischofberger, M. S. Chen, D. B. Medel, C. Y. Tai, W. G. Laver, R. C. Stevens, J. Am. Chem. Soc. 1997, 119, 681-690.
18. Y. S. Babu, P. Chand, S. Bantia, P. Kotian, A. Dehghani, Y. El-Kattan, T. H. Lin, T. L. Hutchison, A. J. Elliot, C. D. Parker, S. L. Ananth, L. L. Horn, G. W. Laver, A. Montgomery, J. Med. Chem. 2000, 43, 3482-3486.
19. H.-P. Hsieh, J. T.-A. Hsu, Curr. Pharm. Des. 2007, 13, 3531-3542.
20. T. Taishi, S. Takechi, S. Mori, Tetrahedron Lett. 1998, 39, 4347-4350.
21. D. T. Ngoc, M. Albicker, L. Schneider, N. Cramer, Org. Biomol. Chem. 2010, 8, 1781-1784.
22. M. Nakatani, M. Nakamura, A. Suzuki, M. Inoue, T. Katoh, Org. Lett. 2002, 4, 4483-4486.
23. K. Watanabe, J. Sakurai, H. Abe, T. Katoh, Chem. Commun. 2010, 46, 4055-4057.
24. T. Oguchi, K. Watanabe, K. Ohkubo, H. Abe, T. Katoh, Chem. Eur. J. 2009, 15, 2826-2845.
25. J. L. Kelly, J. A. Linn, J. W. T. Selway, J. Med. Chem. 1989, 32, 1575-1763.
26. This type of reductive alkylation, originally developed by Stork et al. in the 1960s (for a representative work; see:, G. Stork, P. Rosen, N. Goldman, R. V. Coombs, J. Tsuji, J. Am. Chem. Soc. 1965, 87, 275-286), has been successfully utilized as a crucial step in our total synthesis of marine sesquiterpene quinones and hydroquinones; see:, J. Sakurai, T. Oguchi, K. Watanabe, H. Abe, S. Kanno, M. Ishikawa, T. Katoh, Chem. Eur. J. 2008, 14, 829-837.
27. This reagent system has been known to be effective for sterically hindered ketones, see:, L. Fitjer, U. Quabeck, Synth. Commun. 1985, 15, 855-864.
28. When ethylene acetal 8 was subjected to hydrogenation, the stereoselectivity at C8 was reduced (β-/α-Me: ca. 2:1); this was probably caused by an unfavourable conformational change of the decalin ring. Similar examples of this phenomenon have been reported, see
29. P. Stahl, L. Kissau, R. Mazitschek, A. Huwe, P. Furet, A. Giannis, H. Waldmann, J. Am. Chem. Soc. 2001, 123, 11586-11593.
30. E. P. Locke, S. M. Hecht, Chem. Commun. 1996, 2717-2718.
31. T. Ling, E. Poupon, E. J. Rueden, S. H. Kim, E. Theodorakis, J. Am. Chem. Soc. 2002, 124, 12261-12267.
32. J. An, D. F. Wiemer, J. Org. Chem. 1996, 61, 8775-8779.
33. P. A. Aristoff, A. W. Harison, A. M. Huber, Tetrahedron Lett. 1984, 25, 3955-3958.
34. S. S. Welch, A. S. C. P. Pao, Tetrahedron Lett. 1977, 18, 505-508.
35. G. I. Feutrill, R. N. Mirrington, Aust. J. Chem. 1972, 25, 1719-1723.
36. P. A. Bartlett, W. S. Johnson, Tetrahedron Lett. 1970, 11, 4459-4462.
37. Spartan '08, Wavefunction, Inc., Irvine, CA.
38. B. Douglas, D. McDaniel, J. Alexander, Concepts and Models of Inorganic Chemistry, 3rd ed., Wiley, New York, 1994.
39. Initial attempts to invert the C3 hydroxy group by employing the Mitsunobu procedure were unsuccessful, presumably due to steric factors.
40. [4b]
41. C. M. Harris, J. J. Kibby, J. R. Fehlner, A. B. Raabe, T. A. Barber, T. M. Harris, J. Am. Chem. Soc. 1979, 101, 437-445.
42. General application of this deprotection method is now under investigation in our laboratory and will be reported in due course.