Assembly of digitoxin by gold(I)-catalyzed glycosidation of glycosyl o-alkynylbenzoates

Journal of Organic Chemistry

Volumn 76, Issue 23, 2011, Pages 9748-9756

  Ma, Yuyong ^a   Li, Zhongzhen ^b   Shi, Hefang ^b   Zhang, Jian ^a   Yu, Biao ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b OCEAN UNIVERSITY OF CHINA   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACID-LABILE; GLYCOCONJUGATES; GLYCOSIDATIONS; GLYCOSYL; PROTECTING GROUP;

CATALYSIS; ESTERIFICATION; GOLD; GOLD COMPOUNDS; SUGARS;

GLYCOSYLATION;

ALKYNYL GROUP; BENZOIC ACID DERIVATIVE; BIPHENYL DERIVATIVE; DEOXYSUGAR; DIGITOXIN; GLYCOCONJUGATE; GOLD; SILANE DERIVATIVE; TRISACCHARIDE;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; GLYCOSIDATION; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

BENZOATES; CATALYSIS; DIGITOXIN; GLYCOSIDES; GOLD; MOLECULAR CONFORMATION;

EID: 82155203463     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo201850z     Document Type: Article

References (62)

1. Albrecht, H. P. Cardiac glycosides. In Naturally Occurring Glycosides; Ikan, R., Ed.; John Wiley & Sons Ltd.: New York, 1999; p 83.
2. Deepak, D.; Sirsvastava, S.; Khare, N. K.; Khare, A. Fortschr. Chem. Org. Naturst. 1996, 69, 71
3. Eichhorn, E. J.; Gheorghiade, M. Prog. Cardiovasc. Dis. 2002, 44, 252
4. Hauptman, P. J.; Kelly, R. A. Circulation 1999, 99, 1265.
5. Paula, S.; Tabet, M. R.; Ball, W., Jr. J. Biochem. 2005, 44, 498
6. Dostanic-Larson, I.; van Huysse, J. W.; Lorenz., J. N.; Lingrel, J. B. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 15845
7. Stenkvist, B.; Bengtsson, E.; Eriksson, O.; Holmquist, J.; Nordin, B.; Westman-Naeser, S. Lancet 1979, 1, 563
8. Stenkvist, B.; Bengtsson, E.; Eriksson, O.; Jarkrans, T.; Nordin, B. N. Engl. J. Med. 1982, 306, 484
9. Lopez-Lazaro, M.; Pastor, N.; Azrak, S. S.; Ayuso, M. J.; Austin, C. A.; Cortes, F. J. Nat. Prod. 2005, 68, 1642
10. Langenhan, J. M.; Peters, N. R.; Guzei, I. A; Hoffmann, F. M.; Thorson, J. S. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 12305
11. Langenhan, J. M.; Engle, J. M.; Slevin, L. K.; Fay, L. R.; Lucker, R. W.; Smith, K. R.; Endo, M. M. Bioorg. Med. Chem. Lett. 2008, 18, 670
12. Wang, H.-Y. L.; Rojanasakul, Y.; O'Doherty, G. A. ACS Med. Chem. Lett. 2011, 2, 264
13. Elderfield, R. C.; Uhle, F. C.; Fried, J. J. Am. Chem. Soc. 1947, 69, 2235
14. Zorbach, W. W.; Henderson, N.; Saeki, S. J. Org. Chem. 1964, 29, 2016
15. Meyer zu Reckendorf, M.; Wassiliadou-Micheli, N.; Bischof, E. Chem. Ber 1971, 104, 1
16. Takiura, K.; Yuki, H.; Okamoto, Y.; Takai, H.; Honda, S. Chem. Pharm. Bull. 1974, 22, 2263
17. Albrecht, H. P. Liebigs Ann. Chem. 1977, 1429
18. Thiem, J.; Köpper, S.; Schwentner, J. Liebigs Ann. Chem. 1985, 2135
19. Rathore, H.; Hashimoto, T.; Igarashi, K.; Nukaya, H.; Fullerton, D. S. Tetrahedron 1985, 41, 5427
20. Rathore, H.; Form, A. H. L.; Ahmed, K. J. Med. Chem. 1986, 29, 1945
21. Prisbe, E. J.; Verheyden, J. P. H.; Montgomery, W. W.; Strosberg, A. M. J. Med. Chem. 1986, 29, 239
22. Harreus, A.; Kunz, H. Liebigs Ann. Chem. 1986, 717
23. Templeton, J. F.; Setiloane, P.; Kumar, V. P. S.; Yan, Y.; Zeglam, T. H.; LaBella, F. S. J. Med. Chem. 1991, 34, 2778
24. Templeton, J. F.; Ling, Y.; Zeglam, T. H.; Marat, K.; LaBella, F. S. J. Chem. Soc., Perkin Trans. 1 1992, 2503
25. Luta, M.; Hensel, A.; Kreis, W. Steroid 1998, 63, 44
26. Finizia, G. J. J. Carbohydr. Chem. 1998, 17, 75
27. Tanaka, H.; Sakamoto, H.; Sano, A.; Nakamura, S.; Nakajima, M.; Hashimoto, S. Chem. Commun. 1999, 1259
28. Jesberger, M.; Jaunzems, J.; Jung, A.; Jas, G.; Schonberger, A; Kirschning, A. Synlett 2000, 1289
29. Jaunzems, J.; Jesberger, M.; Sourkouni-Argirusi, G.; Kirschning, A. Angew. Chem, Int. Ed. 2003, 42, 1166
30. Wiesner, K.; Tsai, T. Y. R.; Jin, H. Helv. Chim. Acta 1985, 68, 300
31. Wiesner, K.; Tsai, T. Y. R. Pure Appl. Chem. 1986, 58, 799
32. McDonald, F. E.; Reddy, K. S.; Diaz, Y. J. Am. Chem. Soc. 2000, 122, 4304
33. McDonald, F. E.; Reddy, K. S. Angew. Chem., Int. Ed. 2001, 40, 3653
34. Zhou, M.; O'Doherty, G. A. Org. Lett. 2006, 8, 4339
35. Zhou, M.; O'Doherty, G. A. J. Org. Chem. 2007, 72, 2485
36. Yu, B.; Sun, J. Chem. Asia J. 2009, 4, 642
37. Yu, B.; Zhang, Y.; Tang, P. Eur. J. Org. Chem. 2007, 5145
38. Pellissier, H. Tetrahedron 2004, 60, 5123
39. For a recent review on the glycosylation methods, see: Zhu, X.; Schmidt, R. R. Angew. Chem., Int. Ed. 2009, 48, 1900
40. Li, Y.; Yang, Y.; Yu, B. Tetrahedron Lett. 2008, 49, 3604
41. Li, Y.; Yang, X.; Liu, Y.; Zhu, C.; Yang, Y.; Yu, B. Chem. - Eur. J. 2010, 16, 1871
42. Zhu, Y.; Yu, B. Angew. Chem., Int. Ed. 2011, 50, 8329
43. Zhang, Q.; Sun, J.; Zhu, Y.; Zhang, F.; Yu, B. Angew. Chem., Int. Ed. 2011, 50, 4933
44. Liao, J.; Sun, J.; Niu, Y.; Yu, B. Tetrahedron Lett. 2011, 52, 3075
45. Li, Y.; Sun, J.; Yu, B. Org. Lett. 2011, 13, 5508
46. Marzabadi, C. H.; Frank, R. W. Tetrahedron 2000, 56, 8385
47. Hou, D.; Lowary, T. L. Carbohydr. Res. 2009, 344, 1901
48. Brown, M. A.; Cox, P. J.; Howie, R. A.; Melvin, O. A.; Taylor, O. J.; Wardell, J. L. J. Organomet. Chem. 1995, 498, 275
49. Prins, D. A. J. Am. Chem. Soc. 1948, 70, 3955
50. Baer, H. H.; Hanna, H. R. Carbohydr. Res. 1982, 110, 19
51. Jones, K.; Wood, W. W. J. Chem. Soc., Perkin Trans. 1 1988, 999
52. Klemer, A.; Rodemeyer, G. Chem. Ber. 1974, 107, 2612
53. Horton, D.; Weckerle, W. Carbohydr. Res. 1975, 44, 227
54. Minami, A.; Eguchi, T. J. Am. Chem. Soc. 2007, 129, 5102
55. 2NH, rt, 100%) and saponification (1 N NaOH, THF, 50 °C, 98%); see: Li, Y.; Yang, W.; Ma, Y.; Sun, J.; Shan, L.; Zhang, W.-D.; Yu, B. Synlett 2011, 914
56. Leete, E.; Gregory, H.; Gros, E. G. J. Am. Chem. Soc. 1965, 87, 3475
57. Wilson, W. E.; Johnson, S. A.; Perkins, W. H.; Ripley, J. E. Anal. Chem. 1967, 39, 40
58. Hanessian, S.; Lavallee, P. Can. J. Chem. 1975, 53, 2975
59. Seki, M.; Kondo, K.; Kuroda, T.; Yamanaka, T.; Iwasaki, T. Synlett 1995, 609
60. King, J. F.; Allbutt, A. D. Can. J. Chem. 1970, 48, 1754
61. Lowary, T. L.; Hindsgaul, O. Carbohydr. Res. 1994, 251, 33
62. Ferrier, R. J. J. Chem. Soc., Perkin Trans. 1 1979, 1455