A straightforward and flexible [4 + 2] route to β-C-naphthyl-2-deoxy- glycosides through tandem hydroboration-ketal reduction: De novo access to C-naphthyl-6-fluoro and 6,6-difluoro 2-deoxyglycosides

Journal of Organic Chemistry

Volumn 70, Issue 7, 2005, Pages 2641-2650

  Nguyen, Quang Vu ^a   Leconte, Stéphane ^a   Brown, Eric ^a   Grée, Danielle ^b   Grée, René ^b   Dujardin, Gilles ^a  

^a UNIVERSITÉ DU MAINE   (France)

^b UNIVERSITÉ DE RENNES 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; DERIVATIVES; HYDRATION; SYNTHESIS (CHEMICAL);

DOUBLE BOND; FLUORINATION; KETAL MOIETY;

AROMATIC HYDROCARBONS;

FLUORIDE; GLYCOSIDE; PYRAN DERIVATIVE;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; FLUORINATION; HYDRATION; HYDROBORATION; OXIDATION; REDUCTION; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

GLYCOSIDES; MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION-REDUCTION;

EID: 17044370011     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048042j     Document Type: Article

References (59)

1. Jaramillo, C. Knapp, S. Synthesis 1994, 1.
2. Krohn, K.; Rohr, J. Top. Curr. Chem. 1997, 188, 127.
3. (a) Boyd, V. A.; Sulikowski, G. A. J. Am. Chem. Soc. 1995, 117, 8472.
4. (b) Matsuo, G.; Miki, Y.; Nakata, M.; Matsumura, S.; Toshima, K. J. Org. Chem. 1999, 64, 7101.
5. (c) Krohn, K.; Agocs, A.; Baüerlein, C. J. Carbohydr. Chem. 2003, 7-8, 579.
6. (a) Brimble, M. A.; Brenstrum, T. J. Tetrahedron Lett. 2000, 41, 1107.
7. (b) Brimble, M. A.; Brenstrum, T. J. J. Chem. Soc., Perkin Trans. 1 2001, 41, 1612.
8. (a) Boyd, V. A.; Drake, B. E.; Sulikowski, G. A. J. Org. Chem. 1993, 58, 3191.
9. (b) Andrews, F. L.; Larsen, D. Tetrahedron Lett. 1994, 35, 8693.
10. (c) Hosoya, T.; Ohashi, Y.;; Matsumoto, T.; Suzuki, K. Tetrahedron Lett. 1996, 37, 663.
11. (d) Toshima, K.; Matsuo, I., Ushiki, Y.; Nakata, M.; Matsumura, S. J. Org. Chem. 1998, 63, 2309.
12. (e) Palmicci, E. R.; Seeberger, P. H. Org. Lett. 2001, 3, 1547.
13. For other relevant potential methods, see: (a) Moineau, C.; Bolitt, V.; Sinou, D. J. Org. Chem. 1998, 63, 582. (b) Ramnauth, J.; Poulin, O.; Rakhit, S.; Maddaford, S. P. Org. Lett. 2001, 3, 2013. (c) Rousseau, C.; Martin, O. R. Org. Lett. 2003, 5, 3763.
14. For other relevant potential methods, see: (a) Moineau, C.; Bolitt, V.; Sinou, D. J. Org. Chem. 1998, 63, 582. (b) Ramnauth, J.; Poulin, O.; Rakhit, S.; Maddaford, S. P. Org. Lett. 2001, 3, 2013. (c) Rousseau, C.; Martin, O. R. Org. Lett. 2003, 5, 3763.
15. For other relevant potential methods, see: (a) Moineau, C.; Bolitt, V.; Sinou, D. J. Org. Chem. 1998, 63, 582. (b) Ramnauth, J.; Poulin, O.; Rakhit, S.; Maddaford, S. P. Org. Lett. 2001, 3, 2013. (c) Rousseau, C.; Martin, O. R. Org. Lett. 2003, 5, 3763.
16. (a) Kaelin, D. E., Jr.; Lopez, O. D.; Martin, S. F. J. Am. Chem. Soc. 2001, 123, 6937.
17. (b) Apsel, B.; Bender, J. A.; Escobar, M.; Kaelin, D. E., Jr.; Lopez, O. D.; Martin, S. F. Tetrahedron Lett. 2003, 44, 1075.
18. (c) Kaelin, D. E., Jr.; Sparks, S. M.; Plake, H. R.; Martin, S. F. J. Am. Chem. Soc. 2003, 125, 12994
19. (d) Martin, S. F. Pure Appl. Chem. 2003, 75, 63
20. (e) Chen, C.-L.; Martin, S. F. Org. Lett. 2004, 6, 3581.
21. (a) Fuganti, C.; Serra, S. Synlett 1999, 1241.
22. (b) Paetsch, D.; Dötz, K. H. Tetrahedron Lett. 1999, 487.
23. (c) Pulley, S. R., Carey, J. P. J. Org. Chem. 1998, 63, 5275
24. (d) Parker, K. A.; Georges, A. T. Org. Lett. 2000, 2, 497.
25. (e) Cordero-Vargas, A., Quiclet-Sire, B.; Zard, S. Z. Tetrahedron Lett. 2004, 45, 7335.
26. Collet, S.; Remi, J. F.; Cariou, C.; Laib, S.; Nguyen, Q. V.; Dujardin, G. Tetrahedron Lett. 2004, 45, 4911.
27. Kirschning, A.; Chen, G.; Dräger, G.; Schuberth, I.; Tietze, L. F. Bioorg. Med. Chem. 2000, 8, 2347.
28. Schmidt, R. R.; Frick, W.; Haag-Zeino, B.; Apparao, S. Tetrahedron Lett. 1987, 28, 4045.
29. Hart, D. J.; Merriman, G. H.; Young, D. G. J. Tetrahedron 1996, 14437.
30. (a) Calimente, D.; Postema, M. H. D. J. Org. Chem. 1999, 64, 1770.
31. (b) Schmidt, B.; Org. Lett. 2000, 2, 791.
32. Hauser, F. M.; Hu, X. Org. Lett. 2002, 3, 2977.
33. Martel, A.; Leconte, S.; Dujardin, G.; Brown, E.; Maisonneuve, V.; Retoux, R. Eur. J. Org. Chem. 2002, 514.
34. Nguyen, Q. V.; Gree, D.; Gree, R.; Brown, E.; Dujardin, G. Tetrahedron Lett. 2003, 44, 6425.
35. Boger, D. L.; Robarge, K. D. J. Org. Chem. 1985, 53, 5796.
36. Vijayasaradhi, S.; Aidhen, I. S. Org. Lett. 2002, 4, 1739.
37. 1H NMR NOE measurements (see Table 5).
38. Dujardin, G.; Rossignol, S.; Brown, E. Tetrahedron Lett. 1996, 37, 4007.
39. Coleman, R. S.; Fraser, J. R. J. Org. Chem. 1993, 58, 385.
40. Fleming, B.; Bolker, H. I. Can. J. Chem. 1974, 52, 888.
41. Cossy, J.; Bellosta, V.; Müller, M. C. Tetrahedron Lett. 1992, 33, 5045.
42. (a) Hunter, R.; Bartels, B.; Michael, J. P. Tetrahedron Lett. 1991, 32, 1095.
43. (b) Hunter, R.; Bartels, B. J. Org. Chem. 1993, 58, 6756.
44. 1H NMR correlation with 5a (see Table 5).
45. For some leading references concerning the fruitful incorporation of fluorine in biomolecules, see the following, (a) 14,14-Difluoro4- demethoxidaunorubicin: Matsuda, F.; Matsumoto, T.; Ohsaki, M.; Terashima, S. Tetrahedron Lett. 1989, 30, 4259. (b) 5′-(Trifluoromethyl) anthracycline glycoside: Takagi, Y.; Nakai, K.; Tsuchiya, T.; Yakeuchi, T. J. Med. Chem. 1996, 39, 1582 (c) Vinflunine: Fahy, J.; Duflos, A.; Ribet, J.-P.; Jacquesy, J.-C.; Berrier, C.; Jouannetaud, M.-P.; Zunino, F. J. Am. Chem. Soc. 1997, 119, 8576. (d) α-Fluorophosphono-sugars: Berkowitz, D. B.; Bose, M.; Pfannenstiel, T. J.; Doukov, T. J. Org. Chem 2000, 65, 4498. (e) 14-Fluoro-doxorubicin: Beretonni, M.; Cipollone, A.; Olivieri, L.; Palomba, D.; Arcamone, F.; Maggi, C. A.; Animati, F. Tetrahedron Lett. 2002, 43, 2867. (f) 26-Trifluorodehydrodesoxy epothilone B: Rivkin, A.; Yoshimura, F.; Gabarda, A. E.; Cho, Y. S.; Chou, T.-C.; Dong, H.; Danishefsky, S. J. J. Am. Chem. Soc. 2004, 126, 10913.
46. For some leading references concerning the fruitful incorporation of fluorine in biomolecules, see the following, (a) 14,14-Difluoro4- demethoxidaunorubicin: Matsuda, F.; Matsumoto, T.; Ohsaki, M.; Terashima, S. Tetrahedron Lett. 1989, 30, 4259. (b) 5′-(Trifluoromethyl) anthracycline glycoside: Takagi, Y.; Nakai, K.; Tsuchiya, T.; Yakeuchi, T. J. Med. Chem. 1996, 39, 1582 (c) Vinflunine: Fahy, J.; Duflos, A.; Ribet, J.-P.; Jacquesy, J.-C.; Berrier, C.; Jouannetaud, M.-P.; Zunino, F. J. Am. Chem. Soc. 1997, 119, 8576. (d) α-Fluorophosphono-sugars: Berkowitz, D. B.; Bose, M.; Pfannenstiel, T. J.; Doukov, T. J. Org. Chem 2000, 65, 4498. (e) 14-Fluoro-doxorubicin: Beretonni, M.; Cipollone, A.; Olivieri, L.; Palomba, D.; Arcamone, F.; Maggi, C. A.; Animati, F. Tetrahedron Lett. 2002, 43, 2867. (f) 26-Trifluorodehydrodesoxy epothilone B: Rivkin, A.; Yoshimura, F.; Gabarda, A. E.; Cho, Y. S.; Chou, T.-C.; Dong, H.; Danishefsky, S. J. J. Am. Chem. Soc. 2004, 126, 10913.
47. For some leading references concerning the fruitful incorporation of fluorine in biomolecules, see the following, (a) 14,14-Difluoro4- demethoxidaunorubicin: Matsuda, F.; Matsumoto, T.; Ohsaki, M.; Terashima, S. Tetrahedron Lett. 1989, 30, 4259. (b) 5′-(Trifluoromethyl) anthracycline glycoside: Takagi, Y.; Nakai, K.; Tsuchiya, T.; Yakeuchi, T. J. Med. Chem. 1996, 39, 1582 (c) Vinflunine: Fahy, J.; Duflos, A.; Ribet, J.-P.; Jacquesy, J.-C.; Berrier, C.; Jouannetaud, M.-P.; Zunino, F. J. Am. Chem. Soc. 1997, 119, 8576. (d) α-Fluorophosphono-sugars: Berkowitz, D. B.; Bose, M.; Pfannenstiel, T. J.; Doukov, T. J. Org. Chem 2000, 65, 4498. (e) 14-Fluoro-doxorubicin: Beretonni, M.; Cipollone, A.; Olivieri, L.; Palomba, D.; Arcamone, F.; Maggi, C. A.; Animati, F. Tetrahedron Lett. 2002, 43, 2867. (f) 26-Trifluorodehydrodesoxy epothilone B: Rivkin, A.; Yoshimura, F.; Gabarda, A. E.; Cho, Y. S.; Chou, T.-C.; Dong, H.; Danishefsky, S. J. J. Am. Chem. Soc. 2004, 126, 10913.
48. For some leading references concerning the fruitful incorporation of fluorine in biomolecules, see the following, (a) 14,14-Difluoro4- demethoxidaunorubicin: Matsuda, F.; Matsumoto, T.; Ohsaki, M.; Terashima, S. Tetrahedron Lett. 1989, 30, 4259. (b) 5′-(Trifluoromethyl) anthracycline glycoside: Takagi, Y.; Nakai, K.; Tsuchiya, T.; Yakeuchi, T. J. Med. Chem. 1996, 39, 1582 (c) Vinflunine: Fahy, J.; Duflos, A.; Ribet, J.-P.; Jacquesy, J.-C.; Berrier, C.; Jouannetaud, M.-P.; Zunino, F. J. Am. Chem. Soc. 1997, 119, 8576. (d) α-Fluorophosphono-sugars: Berkowitz, D. B.; Bose, M.; Pfannenstiel, T. J.; Doukov, T. J. Org. Chem 2000, 65, 4498. (e) 14-Fluoro-doxorubicin: Beretonni, M.; Cipollone, A.; Olivieri, L.; Palomba, D.; Arcamone, F.; Maggi, C. A.; Animati, F. Tetrahedron Lett. 2002, 43, 2867. (f) 26-Trifluorodehydrodesoxy epothilone B: Rivkin, A.; Yoshimura, F.; Gabarda, A. E.; Cho, Y. S.; Chou, T.-C.; Dong, H.; Danishefsky, S. J. J. Am. Chem. Soc. 2004, 126, 10913.
49. For some leading references concerning the fruitful incorporation of fluorine in biomolecules, see the following, (a) 14,14-Difluoro4- demethoxidaunorubicin: Matsuda, F.; Matsumoto, T.; Ohsaki, M.; Terashima, S. Tetrahedron Lett. 1989, 30, 4259. (b) 5′-(Trifluoromethyl) anthracycline glycoside: Takagi, Y.; Nakai, K.; Tsuchiya, T.; Yakeuchi, T. J. Med. Chem. 1996, 39, 1582 (c) Vinflunine: Fahy, J.; Duflos, A.; Ribet, J.-P.; Jacquesy, J.-C.; Berrier, C.; Jouannetaud, M.-P.; Zunino, F. J. Am. Chem. Soc. 1997, 119, 8576. (d) α-Fluorophosphono-sugars: Berkowitz, D. B.; Bose, M.; Pfannenstiel, T. J.; Doukov, T. J. Org. Chem 2000, 65, 4498. (e) 14-Fluoro-doxorubicin: Beretonni, M.; Cipollone, A.; Olivieri, L.; Palomba, D.; Arcamone, F.; Maggi, C. A.; Animati, F. Tetrahedron Lett. 2002, 43, 2867. (f) 26-Trifluorodehydrodesoxy epothilone B: Rivkin, A.; Yoshimura, F.; Gabarda, A. E.; Cho, Y. S.; Chou, T.-C.; Dong, H.; Danishefsky, S. J. J. Am. Chem. Soc. 2004, 126, 10913.
50. For some leading references concerning the fruitful incorporation of fluorine in biomolecules, see the following, (a) 14,14-Difluoro4- demethoxidaunorubicin: Matsuda, F.; Matsumoto, T.; Ohsaki, M.; Terashima, S. Tetrahedron Lett. 1989, 30, 4259. (b) 5′-(Trifluoromethyl) anthracycline glycoside: Takagi, Y.; Nakai, K.; Tsuchiya, T.; Yakeuchi, T. J. Med. Chem. 1996, 39, 1582 (c) Vinflunine: Fahy, J.; Duflos, A.; Ribet, J.-P.; Jacquesy, J.-C.; Berrier, C.; Jouannetaud, M.-P.; Zunino, F. J. Am. Chem. Soc. 1997, 119, 8576. (d) α-Fluorophosphono-sugars: Berkowitz, D. B.; Bose, M.; Pfannenstiel, T. J.; Doukov, T. J. Org. Chem 2000, 65, 4498. (e) 14-Fluoro-doxorubicin: Beretonni, M.; Cipollone, A.; Olivieri, L.; Palomba, D.; Arcamone, F.; Maggi, C. A.; Animati, F. Tetrahedron Lett. 2002, 43, 2867. (f) 26-Trifluorodehydrodesoxy epothilone B: Rivkin, A.; Yoshimura, F.; Gabarda, A. E.; Cho, Y. S.; Chou, T.-C.; Dong, H.; Danishefsky, S. J. J. Am. Chem. Soc. 2004, 126, 10913.
51. Hayman, C. M.; Larsen, D. S.; Brooker, S. Aust. J. Chem. 1998, 51, 545.
52. Denmark, S. E.; Stavenger, R. A. J. Org. Chem. 1998, 63, 9523.
53. Lal, G. S.; Pez, G. P.; Pesaresi, R. J., Prozonic, F. M., Cheng, H. J. Org. Chem. 1999, 64, 7048.
54. (a) Middleton, W. J. J. Org. Chem. 1975, 40, 4.
55. For a recent representative example, see: (b) De Jonghe, S.; Van Overmeire, I.; Poulton, S.; Hendrix, C.; Busson, R.; Van Caulenbergh, S.; De Keukeleire, D.; Spiegel, S.; Herdewinjn, P. Bioorg. Med. Chem. Lett. 1999, 93, 171.
56. (a) Ohba, T.; Ikeba, E.; Takei, H. Bioorg. Med. Chem. Lett. 1996, 6, 1875.
57. (b) Box, J. M.; Harwood: L. M. Synlett 1997, 571.
58. Prakesh, M.; Kerouderan, E.; Grée, D.; Grée, R.; DeChancie, J.; Houk, K. N. J. Fluorine Chem. 2004, 537.
59. 14 demonstrated that 2-vinylnaphthalene displays no reactivity towards heterodiene 1.