Dihydroxylation of vinyl sulfones: Stereoselective synthesis of (+)- and (-)-febrifugine and halofuginone

Journal of Organic Chemistry

Volumn 75, Issue 2, 2010, Pages 518-521

  McLaughlin, Noel P ^a   Evans, Paul ^a  

^a UNIVERSITY COLLEGE DUBLIN   (Ireland)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIANGIOGENIC; ASYMMETRIC DIHYDROXYLATION; BUILDING BLOCKES; CHEMICAL EQUATIONS; DIHYDROXYLATION; ENANTIOMERIC EXCESS; FEBRIFUGINE; FUNCTIONALIZED; HALOFUGINONE; NATURALLY OCCURRING; STEREOSELECTIVE SYNTHESIS; VINYL SULFONES;

STEREOSELECTIVITY;

FEBRIFUGINE; HALOFUGINONE;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS; STEREOCHEMISTRY;

CATALYSIS; HYDROXYLATION; MOLECULAR STRUCTURE; PIPERIDINES; QUINAZOLINES; QUINAZOLINONES; STEREOISOMERISM; SULFONES;

EID: 75349100933     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo902396m     Document Type: Article

References (59)

1. (a) Koepfli, J. B.; Mead, J. F.; Brockman, J. A., Jr. J. Am. Chem. Soc. 1947, 69, 1837.
2. (b) Kuehl, F. A., Jr.; Spencer, C. F.; Folkers, K. J. Am. Chem. Soc. 1948, 70, 2091.
3. (c) Koepfli, J. B.; Mead, J. F.; Brockman, J. A., Jr. J. Am. Chem. Soc. 1949, 71, 1048.
4. (d) Koepfli, J. B.; Brockman, J. A., Jr.; Moffat, J. J. Am. Chem. Soc. 1950, 72 3323.
5. (e) Ablondi, F.; Gordon, S.; Morton, J., II; Williams, J. H. J. Org. Chem. 1952, 17, 14.
6. (a) Wiesner, J.; Ortmann, R.; Jomaa, H.; Schlitzer, M. Angew. Chem., Int. Ed. 2003, 42, 5274.
7. (b) Mital, A. Curr. Med. Chem. 2007, 14, 759.
8. (c) Kumar, V.; Mahajan, A.; Chibale, K. Bioorg. Med. Chem. 2009, 17, 2236.
9. Jiang, S.; Zeng, Q.; Gettayacamin, M.; Tungtaeng, A.; Wannaying, S.; Lim, A.; Hansukjariya, P.; Okunji, C. O.; Zhu, S.; Fang, D. Antimicrob. Agents Chemother. 2005, 49, 1169.
10. (a) Barringer, D. F., Jr.; Berkelhammer, G.; Carter, S. D.; Goldman, L.; Lanzilotti, A. E. J. Org. Chem. 1973, 38, 1933.
11. (b) Barringer, D. F., Jr.; Berkelhammer, G.; Wayne, R. S. J. Org. Chem. 1973, 38, 1937.
12. Baker, B. R.; Schaub, R. E.; McEvoy, F. J.; Williams, J. H. J. Org. Chem. 1952, 17, 132 and references cited therein.
13. Kobayashi, S.; Ueno, M.; Suzuki, R.; Ishitani, H.; Kim, H.-S.; Wataya, Y. J. Org. Chem. 1999, 64, 6833.
14. For recent syntheses of 1 and 2 see: (a) Katoh, M.; Matsune, R.; Nagase, H.; Honda, T. Tetrahedron Lett. 2004, 45, 6221.
15. (b) Katoh, M.; Matsune, R.; Honda, T. Heterocycles 2006, 67, 189.
16. (c) Burgess, L. E.; Gross, E. K. M.; Jurka, J. Tetrahedron Lett. 1996, 37, 3255.
17. (d) Takeuchi, Y.; Azuma, K.; Takakura, K.; Abe, H.; Harayama, T. Chem. Commun. 2000, 1643.
18. (e) Takeuchi, Y.; Azuma, K.; Takakura, K.; Abe, H.; Kim, H.-S.; Wataya, Y.; Harayama, T. Tetrahedron 2001, 57, 1213.
19. (f) Takeuchi, Y.; Oshige, M.; Azuma, K.; Abe, H.; Harayama, T. Chem. Pharm. Bull. 2005, 53, 868.
20. (g) Taniguchi, T.; Ogasawara, K. Org. Lett. 2000, 2, 3193.
21. (h) Ooi, H.; Urushibara, A.; Esumi, T.; Iwabuchi, Y.; Hatakeyama, S. Org. Lett. 2001, 3, 953.
22. (i) Huang, P.-Q.; Wei, B.-G.; Ruan, Y.-P. Synlett 2003, 1663.
23. (j) Liu, R.-C.; Huang, W.; Ma, J.-Y.; Wei, B.-G.; Lin, G.-Q. Tetrahedron Lett. 2009, 50, 4046.
24. (k) Michael, J. P.; de Koning, C. B.; Pienaar, D. P. Synlett 2006, 383.
25. (l) Wee, A. G. H.; Fan, G.-J. Org. Lett. 2008, 10, 3869.
26. (m) Sukemoto, S.; Oshige, M.; Sato, M.; Mimura, K.-I.; Nishioka, H.; Abe, H.; Harayama, T.; Takeuchi, Y. Synthesis 2008, 3081.
27. (n) Sieng, B.; Ventura, O. L.; Bellosta, V.; Cossy, J. Synlett 2008, 1216.
28. (o) Sudhakar, N.; Srinivasulu, G.; Rao, G. S.; Rao, B. V. Tetrahedron: Asymmetry 2008, 19, 2153.
29. (p) Wijdeven, M. A.; van den Berg, R. J. F.; Wijtmans, R.; Botman, P. N. M.; Blaauw, R. H.; Schoemaker, H. E.; van Delft, F. L.; Rutjes, F. P. J. T. Org. Biomol. Chem. 2009, 7, 2976.
30. (q) Chen, W.; Liebeskind, L. S. J. Am. Chem. Soc. 2009, 131, 12546.
31. (r) Ashoorzadeh, A.; Caprio, V. Synlett 2005, 346.
32. (s) Ashoorzadeh, A.; Archibald, G.; Caprio, V. Tetrahedron 2009, 65, 4671.
33. (t) Emmanuvel, L.; Kamble, D. A.; Sudalai, A. Tetrahedron: Asymmetry 2009, 20, 84.
34. (a) Hirai, S.; Kikuchi, H.; Kim, H.-S.; Begum, K.; Wataya, Y.; Tasaka, H.; Miyazawa, Y.; Yamamoto, K.; Oshima, Y. J. Med. Chem. 2003, 46, 4351.
35. (b) Zhu, S.; Zhang, Q.; Gudise, C.; Wei, L.; Smith, E.; Zeng, Y. Bioorg. Med. Chem. 2009, 17, 4496.
36. (c) Zhu, S.; Meng, L.; Zhang, Q.; Wei, L. Bioorg. Med. Chem. Lett. 2006, 16, 1854.
37. (d) Kikuchi, H.; Yamamoto, K.; Horoiwa, S.; Hirai, S.; Kasahara, R.; Hariguchi, N.; Matsumoto, M.; Oshima, Y. J. Med. Chem. 2006, 49, 4698.
38. (e) Linder, M. R.; Heckeroth, A. R.; Najdrowski, M.; Daugschies, A.; Schollmeyer, D.; Miculka, C. Bioorg. Med. Chem. Lett. 2007, 17, 4140.
39. (a) Angel, S.; Weinberg, Z. G.; Polishuk, O.; Heit, M.; Plavnik; Bartov, I. Poultry Sci. 1985, 64, 294-296.
40. (b) Granot, I.; Bartov, I.; Plavnik, I.; Wax, E.; Hurwitz, S.; Pines, M. Poultry Sci. 1991, 70, 1559.
41. Yee, K. O.; Connolly, C. M.; Pines, M.; Lawler, J. Cancer Biology Therapy 2006, 5, 218.
42. de Jonge, M. J. A.; Dumez, H.; Verweij, J.; Yarkoni, S.; Snyder, D.; Lacombe, D.; Marréaud, S.; Yamaguchi, T.; Punt, C. J. A.; van Oosterom, A. Eur. J. Cancer 2006, 42, 1768.
43. For review literature see: (a) Michael, J. P. Nat. Prod. Rep. 2008, 25, 139.
44. (b) O'Hagan, D. Nat. Prod. Rep. 2000, 17, 435.
45. (c) Buffat, M. G. P. Tetrahedron 2004, 60, 1701 and references cited therein.
46. Evans, P.; Leffray, M. Tetrahedron 2003, 59, 7973.
47. Au, C. W. G.; Pyne, S. G. J. Org. Chem. 2006, 71, 7097.
48. (a) Carretero, J. C.; Arrayás, R. G. J. Org. Chem. 1998, 63, 6221-6223.
49. (b) Xiao, X.; Antony, S.; Kohlhagen, G.; Pommier, Y.; Cushman, M. Bioorg. Med. Chem. 2004, 12, 5147.
50. (c) Macdonald, S. J. F.; Belton, D. J.; Buckley, D. M.; Spooner, J. E.; Anson, M. S.; Harrison, L. A.; Mills, K.; Upton, R. J.; Dowle, M. D.; Smith, R. A.; Molloy, C. R.; Risley, C. J. Med. Chem. 1998, 41, 3919.
51. (d) Evans, P.; Johnson, P.; Taylor, R. J. K. Eur. J. Org. Chem. 2006, 1740.
52. For a report that cis-24 undergoes conversion to the corresponding 2,5-disubstituted furan under Lewis acidic conditions see: Takeuchi, Y.; Azuma, K.; Abe, H.; Harayama, T. Heterocycles 2000, 53, 2247.
53. For representative references concerning the diastereoselective reaction of allylic systems see: (a) Gung, B. W.; Francis, M. B. J. Org. Chem. 1993, 58, 6177.
54. (b) Gung, B. W.; Francis, M. B. Tetrahedron Lett. 1995, 36, 2579.
55. (c) Evans, D. A.; Kaldor, S. W. J. Org. Chem. 1990, 55, 1698.
56. (d) Houk, K. N.; Paddon-Row, M. N.; Rondan, N. G.; Wu, Y.-D.; Brown, F. K.; Spellmeyer, D. C.; Metz, J. T.; Li, Y.; Loncharich, J. Science 1986, 231, 1108.
57. Stereochemistry assigned based on data reported for cis-25: Okitsu, O.; Suzuki, R.; Kobayashi, S. J. Org. Chem. 2001, 66, 809.
58. Kolb, H. C.; VanNiewenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
59. Obtained from Credimate Trading Ltd.: http://www.credimate.com.