Asymmetric dihydroxylation of D-glucose derived α,β-unsaturated ester: Synthesis of azepane and nojirimycin analogues

Journal of Organic Chemistry

Volumn 69, Issue 14, 2004, Pages 4760-4766

  Dhavale, Dilip D ^a   Markad, Shankar D ^a   Karanjule, Narayan S ^a   PrakashaReddy, J ^b  

^a UNIVERSITY OF PUNE   (India)

^b NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; ESTERS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

DIHYDROXYLATION; STEREOSELECTIVE NUCLEOPHILIC RINGS; VICINAL DIOLS;

GLUCOSE;

ALCOHOL DERIVATIVE; AMINOALCOHOL; AMINOHEPTITOL DERIVATIVE; AMINOSUGAR; AZEPANE; DIOL DERIVATIVE; ESTER; GLUCOSE; NOJIRIMYCIN; NOJIRIMYCIN DERIVATIVE; SODIUM AZIDE; SULFATE; UNCLASSIFIED DRUG;

ARTICLE; DIASTEREOISOMER; DIHYDROXYLATION; REDUCTION; RING OPENING; STEREOCHEMISTRY;

AZEPINES; CATALYSIS; ESTERS; GLUCOSAMINE; GLUCOSE; HYDROXYLATION; INDICATORS AND REAGENTS; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 3042740963     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049509t     Document Type: Article

References (69)

1. (a) Kobayashi, S.; Endo, M.; Nagayama, S. J. Am. Chem. Soc. 1999, 121, 11229-11230.
2. (b) Costas, M.; Adrianne, K.; Chen, T. K.; Jo, D. H.; Que, L. J. Am. Chem. Soc. 2001, 123, 6722-6723.
3. (c) Salvadori, P.; Pini, D.; Petri, A. J. Am. Chem. Soc. 1997, 119, 6929-6930.
4. (d) Bergstad, K.; Jonsson, S. Y.; Backvall, J. E. J. Am. Chem. Soc. 1999, 121, 10424-10425.
5. (e) Ahrgren, L.; Sutin, L. Org. Process Res. Dev. 1997, 1, 425-427.
6. (a) Masaya, S.; Yoshihiko, I. Chem. Rev. 1992, 92, 857-871.
7. (b) Corey, E. J.; Noe, M. C.; Sarshar S. J. Am. Chem. Soc. 1993, 115, 3828-3829.
8. (c) Kolb, H. C.; Van Nieuwenhe, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483-2547.
9. (d) Bennani, Y. L.; Hanessian, S. Chem. Rev. 1997, 97, 3161-3196.
10. (a) Boivin, T. L. B. Tetrahedron 1987, 43, 3309-3662.
11. (b) Gao, Y.; Sharpless, K. B. J. Am. Chem. Soc. 1988, 110, 7538-7539.
12. (c) Zeigler, F. E.; Wang, Y. J. Org. Chem. 1998, 63, 7920-7930.
13. (d) Ko, S. Y. J. Org. Chem. 2092, 67, 2689-2691.
14. (e) Xiong, C.; Wang, W.; Hruby, V. J. J. Org. Chem. 2002, 67, 3514-3517.
15. (f) Fernandes, R. A.; Bodas, M. S.; Kumar, P. Tetrahedron 2002, 58, 1223-1227.
16. (g) Kim, S.; Ko, H.; Kim, E.; Kim, D. Org. Lett. 2002, 4, 1343-1345.
17. (h) Qin, D. G.; Zha, H. Y.; Yao, Z. J. J. Org. Chem. 2002, 67, 1038-1040.
18. (i) Feng, Z.; Zhou, W. Tetrahedron Lett. 2003, 44, 493-495.
19. (j) Garcia-Granados, A.; Lopez, P. E.; Melguizo, E.; Moliz, J. N.; Parra, A.; Simeo, Y.; Dobado, J. A. J. Org. Chem. 2003, 68, 4833-4844.
20. (a) Inouye, S.; Tsuruoka, T.; Ito, T.; Niida, T. Tetrahedron 1968, 24, 2125-2144.
21. (b) Iida, H.; Yamazaki, N.; Kibayashi, C. J. Org. Chem. 1987, 52, 3337-3342.
22. (c) Aoyagi, S.; Fujimaki, S.; Yamazaki, N.; Kibayashi, C. J. Org. Chem. 1991, 56, 815-819.
23. (d) Kajimoto, T.; Liu, K. K. C.; Pederson, R. L.; Zhong, Z.; Ichikawa, Y., Jr.; Porco, J. A.; Wong, C. H. J. Am. Chem. Soc. 1991, 113, 6187-6196.
24. (e) Fairbanks, A. J.; Carpentor, N. C.; Fleet, G. W. J.; Ramsden, N. G.; Cenci de Bello, I.; Winchester, B. G.; Al-Daher, S. S.; Nagahashi, G. Tetrahedron, 1992, 48, 3365-3376.
25. (f) Grandel, R.; Kazmaier, U. Tetrahedron Lett. 1997, 38, 8009-8012.
26. (g) Barili, P. L.; Berti, G.; Catelani, G.; D'Andrea, F.; De Rensis, F.; Ruccioni, L. Tetrahedron 1997, 53, 3409-3416.
27. (h) Xu, Y.; Zhou, W. J. Chem. Soc., Perkin Trans. 1 1997, 1, 741-746.
28. (i) Asano, N.; Kato, A.; Miyauchi, M.; Kizu, H.; Kameda, Y.; Watson, A. A.; Nash, R. J.; Fleet, G. W. J. J. Nat. Prod. 1998, 61, 625-628.
29. (j) Uriel, C.; Santoyo-Gonzalez, F. Synlett 1999, 5993-5995.
30. (k) Godin, G.; Compain, P.; Masson, G.; Martin, O. R. J. Org. Chem. 2002, 67, 6960-6970.
31. (l) Bols, M.; Lillelund, V. H.; Jensen, H. H.; Liang, X. Chem. Rev. 2002, 102, 515-554.
32. (m) Pino-Gonzalez, M. S.; Assiego, C.; Loez-Herrera, F. J. Tetrahedron Lett. 2003, 44, 8353-8356.
33. (n) Somfai, P.; Marchand, P.; Torsell, S.; Lindstrom, U. M. Tetrahedron 2003, 59, 1293-1299.
34. (o) Singh, O. V.; Han, H. Tetrahedron Lett. 2003, 44, 2387-2391.
35. (p) Ko, H.; Kim, E.; Park, J. E.; Kim, D.; Kim, S. J. Org. Chem. 2004, 69, 112-121.
36. (a) Lampe, J. W.; Hughes, P. F.; Biggers, C. K.; Smith, S. H.; Hu, H. J. Org. Chem. 1994, 59, 5147-5148.
37. (b) Lohray, B. B.; Jayamma, Y.; Chatterjee, M. J. Org. Chem. 1995, 60, 5958-5960.
38. (c) Lampe, J. W.; Hughes, P. F.; Biggers, C. K.; Smith, S. H.; Hu, H. J. Org. Chem. 1996, 61, 4572-4581.
39. (d) Johnson, H. A.; Thomas, N. R. Bioorg. Med. Chem. Lett. 2002, 12, 237-241.
40. (e) Assiego, C.; Pino-Gonzalez, M. S.; Lopez-Herrera, F. J. Tetrahedron Lett. 2004, 45, 2611-2613.
41. (a) Elbein, A. D. Annu. Rev. Biochem. 1987, 56, 497-534.
42. (b) Karpas, A.; Fleet, G. W. J.; Dwek, R. A.; Petursson, S.; Namgoong, S. K.; Ramsden, N. G.; Jacob, G. S.; Rademacher, T. W. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 9229-9233.
43. Karpas, A.; Fleet, G. W. J.; Dwek, R. A.; Petursson, S.; Namgoong, S. K.; Ramsden, N. G.; Jacob, G. S.; Rademacher, T. W. FEBS Lett. 1988, 237, 128-132.
44. (c) Fleet, G. W. J. Chem. Brit. 1989, 287-292.
45. (d) Winchester, B.; Fleet, G. W. J. Glycobiology 1992, 2, 199-210.
46. (e) Hughes, A. B.; Rudge, A. J. J. Nat. Prod. Rep. 1994, 11, 135.
47. (f) Merror, Y. L.; Poitout, L.; Deepazy, J.; Dosbaa, I.; Geoffroy, S.; Foglietti, M. Bioorg. Med. Chem. 1997, 5, 519-533.
48. (g) Sears, P.; Wong, C. H. J. Chem. Soc., Chem Commun. 1998, 1161.
49. (h) Butters, T. D.; Van den Brock, L. A. G. M.; Fleet, G. W. J.; Krulle, T. M.; Wormold, M. R.; Dwek, R. A.; Platt, F. M. Tetrahedron: Asymmetry 2000, 11, 113-124.
50. (i) Stuts, A. E. Iminosugars as Glycosidase Inhibitors. Nojirimycin and Beyond; Wiley/VCH: Weinheim, Germany, 1999.
51. (a) Dhavale, D. D.; Desai, V. N.; Sindkhedkar, M.; Mali, R. S.; Castellari, C.; Trombini, C. Tetrahedron: Asymmetry 1997, 8, 1475-1486.
52. (b) Dhavale, D. D.; Saha, N. N.; Desai, V.N.J. Org. Chem. 1997, 62, 7482-7484.
53. (c) Desai, V. N.; Saha, N. N.; Dhavale, D. D. J. Org. Chem. 1999, 64, 1715-1719.
54. (d) Desai, V. N.; Saha, N. N.; Dhavale, D. D. J. Chem. Soc., Chem. Commun. 1999, 1719-1720.
55. (e) Saha, N. N.; Desai, V. N.; Dhavale, D. D. Tetrahedron 2001, 57, 39-46.
56. (f) Patil, N. T.; Tilekar, J. N.; Dhavale, D. D. J. Org. Chem. 2001, 66, 1065-1074.
57. (g) Patil, N. T.; Tilekar, J.; Dhavale, D. Tetrahedron Lett. 2001, 42, 747-749.
58. (h) Dhavale, D. D.; Patil, N. T.; John, S.; Sabharwal, S. Bioorg. Med. Chem. 2002, 10, 2155-2160.
59. (i) Dhavale, D. D.; Saha, N. N.; Desai, V. N.; Tilekar, J. N. Arkivoc 2002, 8, 91-105.
60. (j) Tilekar, J. N.; Patil, N. T.; Jadhav, H. S.; Dhavale, D. D. Tetrahedron 2003, 59, 1873-1876.
61. (k) Dhavale, D. D.; Chaudhari, V. D.; Tilekar, J. N. Tetrahedron Lett. 2003, 44, 7321-7323.
62. (a) Asano, K.; Yasuda, K.; Kizu, H.; Kato, A.; Fan, J.; Nash, R. J.; Fleet, W. J.; Molyneux, R. J. Eur. J. Biochem. 2001, 268, 35-41.
63. (b) Yamashita, T.; Yasuda, K.; Kizu, H.; Kameda, Y.; Watson, A. A.; Nash, R. J.; Fleet, G. W. J.; Asano, N. J. Nat. Prod. 2002, 65, 1875-1881.
64. Although compound 2d is reported in the literature, its NMR study and conformational aspects are not known. It is reported that 2d possesses moderate to high inhibitory activity against almond β-D-glucosidase and bovine liver β-D-galactosidase (a) Noritaka, C.; Yuka, F.; Hiroyuki, I.; Seiichiro, O. Carbohydr. Res. 1992, 237, 185-194.
65. (b) Schaller, C.; Vogel, P.; Jager, V. Carbohydr. Res. 1998, 314, 25-35.
66. (a) Cha, J. K.; Christ, W. J.; Kishi, Y. Tetrahedron 1984, 40, 2247-2255.
67. (b) Brimacombe, J. S.; Kabir, A. K. M. S. Carbohydr. Res. 1986, 150, 35-51.
68. (c) Jarosz, S. Carbohydr. Res. 1988, 183, 209-215.
69. In these particular experiments, triacetylated products were obtained as a mixture of two compounds one with free C3-OH and other with C3-OCHO. Our attempts to separate the mixture were unsuccessful. Therefore, we directly converted the triacetylated products to corresponding hydrochlorides.