Asymmetric synthesis of triacetyl-d-erythro-sphingosine and D-1-deoxyallonojirimycin via Miyashita C2 selective endo-mode azide opening of 2,3-epoxy alcohol

Tetrahedron

Volumn 65, Issue 51, 2009, Pages 10701-10708

  Sridhar, R ^a   Srinivas, B ^a   Rao, K Rama ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

1 DEOXYALLONOJIRIMYCIN; 1 DEOXYGULONOJIRIMYCIN; 1 DEOXYMANNONOJIRIMYCIN; 1 DEOXYNOJIRIMYCIN; ALCOHOL; AZIDE; ENZYME INHIBITOR; SPHINGOSINE DERIVATIVE; TRIACETYL DEXTRO ERYTHRO SPHINGOSINE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENZYME INHIBITION; EPOXIDATION; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; RING CLOSING METATHESIS; SYNTHESIS;

EID: 70449499055     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.10.035     Document Type: Article

References (79)

1. Sasaki M., Tanino K., Hirai A., and Miyashita M. Org. Lett. 5 (2003) 1789
2. Tomata Y., Sasaki M., Tanino K., and Miyashita M. Tetrahedron Lett. 44 (2003) 8975
3. Rogers E.W., and Molinski T.F. Org. Lett. 9 (2007) 437
4. Riethmuller J., Riehle A., Grassme H., and Gulbins E. Biochim. Biophys. Acta 1758 (2006) 2139
5. Snook C.F., Jones J.A., and Hannun Y.A. Biochim. Biophys. Acta 1761 (2006) 927
6. Kester M., and Kolesnick R. Pharm. Res. 47 (2003) 365
7. Rosen H., and Liao J. Curr. Opin. Chem. Biol. 7 (2003) 461
8. Summers S.A., and Nelson D.H. Diabetes 54 (2005) 591
9. Modrak D.E., Gold D.V., and Goldenberg D.M. Mol. Cancer Ther. 5 (2006) 200
10. Zhou S., Zhou H., Walian P.J., and Jap B.K. Biochemistry 46 (2007) 2553
11. Kolter T., and Sandhoff K. Biochim. Biophys. Acta 1758 (2006) 2057
12. Karlsson K.A. Trends Pharmacol. Sci. 12 (1991) 265
13. Hannun Y., and Bell R.M. Science 243 (1989) 500
14. Hannun Y. Science 274 (1996) 1855
15. Kolter T., and Sandhoff K. Angew. Chem., Int. Ed. 38 (1999) 1532
16. Sawatzki P., and Kolter T. Eur. J. Org. Chem. (2004) 3693
17. Koskinen P.M., and Koskinen A.M.P. Synthesis (1998) 1075
18. Howell A.R., and Ndakala A.J. Curr. Org. Chem. 6 (2002) 365
19. Chun J., Lee G., Byun H.-P., and Bittman R. Tetrahedron Lett. 43 (2002) 375
20. Yadav J.S., Geetha V., Raju A.K., Gnaneshwar D., and Chandrasekhar S. Tetrahedron Lett. 44 (2003) 2983
21. Lombardo M., Capdevila M.G., Pasi F., and Trombini C. Org. Lett. 8 (2006) 3303
22. Lee J.-M., Lim H.-S., and Chung S.-K. Tetrahedron: Asymmetry 13 (2002) 343
23. Luo S.-Y., Thopate S.R., Hsu C.-Y., and Hung S.-C. Tetrahedron Lett. 23 (2002) 4889
24. Chaudhari V.D., Kumar K.S.A., and Dhavale D.D. Org. Lett. 7 (2005) 5805
25. Lin C.-C., Fan G.-T., and Fan J.-M. Tetrahedron Lett. 44 (2003) 5281
26. Chiu H.-Y., Tzou D.-L.M., Patkar L.N., and Lin C.-C. J. Org. Chem. 68 (2003) 5788
27. Plettenburg O., Bodmer-Narkevich V., and Wong C.-H. J. Org. Chem. 67 (2002) 4559
28. Llaveria J., Diaz Y., Isabel Matheu M., and Castillon S. Org. Lett. 11 (2009) 205
29. Yoon H.J., Kim Y.-W., Lee B.K., Lee W.K., Kim Y., and Ha Y.-J. Chem. Commun. (2007) 79
30. Righi G., Ciambrone S., D'Achille C., Leonelli A., and Bonini C. Tetrahedron 62 (2006) 11821
31. Enders D., Palecek J., and Grondal C. Chem. Commun. (2006) 655
32. He L., Byun H.-S., and Bittman R. J. Org. Chem. 65 (2000) 7618
33. Cai Y., Ling C.-C., and Bundle D.R. Org. Biomol. Chem. 4 (2006) 1140
34. Paulsen H. Iminosugars as Glycosidase Inhibitors (2004), Wiley-VCH, Germany p. 1
35. Elbein A.D. Annu. Rev. Biochem. 56 (1987) 497
36. Legler G. Adv. Carbohydr. Chem. Biochem. 48 (1990) 319
37. Wrodnigg T.M., Steiner A.J., and Ueberbacher B.J. Anti- Cancer Agents Med. Chem. 8 (2008) 77
38. Yoshikuni Y., Ezure Y., Seto T., Mori K., Watanabe M., and Enomoto H. Chem. Pharm. Bull. 37 (1989) 106
39. Kimura M., Chen F.-J., Nakashima N., Kimura I., Asano N., and Koya S.J. Trad. Med. 12 (1995) 214
40. Robina I., Moreno-Vargas A.J., Carmona A.T., and Vogel P. Curr. Drug Metab. 5 (2004) 329
41. Butters T.D., Dwek R.A., and Platt F.M. Chem. Rev. 100 (2000) 4683
42. Fan J.-Q. Trends Pharmacol. Sci. 24 (2003) 355
43. Bols M. Acc. Chem. Res. 31 (1998) 1
44. In: Stutz A.E. (Ed). Iminosugars as Glycosidase Inhibitors. Nojirimycin and Beyond (1999), Wiley-VCH, Weinheim, Germany
45. For recent publications see:
46. Racine E., Bello C., Lemaire S.G., Vogel P., and Sandrine P. J. Org. Chem. 74 (2009) 1766
47. Song X., and Hollingsworth R.I. Tetrahedron Lett. 48 (2007) 3115
48. Takahata H., Banba Y., Sasatani M., Nemoto H., Kato A., and Adachi I. Tetrahedron 60 (2004) 8199
49. Saha N.N., Desai V.N., and Dhavale D.D. Tetrahedron 57 (2001) 39
50. Comins D.L., and Fulp A.B. Tetrahedron Lett. 42 (2001) 6839
51. Yokoyama H., Otaya K., Kobayashi H., Miyazawa M., Yamaguchi S., and Hirai Y. Org. Lett. 2 (2000) 2427
52. Asano N., Oseki K., Kizu H., and Matsui K. J. Med. Chem. 37 (1994) 3701
53. Previous synthesis of allo-DNJ.
54. Guaragna A., D'Errico S., D'Alonzo D., Pedatella S., and Palumbo G. Org. Lett. 9 (2007) 3473
55. Hong B.-C., Chen Z.-Y., Nagarajan A., Kottani R., Chavan V., Chen W.-H., Jiang Y.-F., Zhang S.-C., Liao J.-H., and Sarshar S. Carbohydr. Res. 340 (2005) 2457
56. Kato A., Kato N., Kano E., Adachi I., Ikeda K., Yu L., Okamato T., Banba Y., Ouchi H., Takahata H., and Asano N. J. Med. Chem. 48 (2005) 2036
57. Singh O.V., and Han H. Tetrahedron Lett. 44 (2003) 2387
58. Asano K., Hakogi T., Iwama S., and Katsumura S. Chem. Commun. (1999) 41
59. Nicolaou K.C., Prasad C.V.C., Somers P.K., and Hwang C.K. J. Am. Chem. Soc. 111 (1989) 5335
60. Millar J.G., and Oehlschlager A.C. J. Org. Chem. 49 (1984) 2332
61. Katsuki T., and Sharpless K.B. J. Am. Chem. Soc. 102 (1980) 5974
62. Pfenninger A. Synthesis (1986) 89
63. Baker S.R., Boot J.R., Molgan S.E., Osborne D.T., Ross W.J., and Shrubsall P.R. Tetrahedron Lett. 24 (1983) 4469
64. Hayes C.J., Sherlock A.E., Green M.P., Wilson C., Blake A.J., Selby M.D., and Prodger J.C. J. Org. Chem. 73 (2008) 2041
65. Reddy M.S., Narender M., Nageswar Y.V.D., and Rao K.R. Synlett (2006) 1110
66. Abraham E., Davies S.G., Millican N.L., Nicholson R.L., Roberts P.M., and Smith A.D. Org. Biomol. Chem. 6 (2008) 1655
67. Disadee W., and Ishikawa T. J. Org. Chem. 70 (2005) 9399
68. Findeis M.A., and Whitesides G.M. J. Org. Chem. 52 (1987) 2838
69. Blanchette M.A., Choy W., Davis J.T., Essenfeld A.P., Masamune S., Roush W.R., and Sakai T. Tetrahedron Lett. 25 (1984) 2183
70. Grubbs R.H., and Chang S. Tetrahedron 54 (1998) 4413
71. Furstner A. Angew. Chem., Int. Ed. 39 (2000) 3013
72. Trnka T.M., and Grubbs R.H. Acc. Chem. Res. 34 (2001) 18
73. Nicolaou K.C., Bulger P.G., and Sarlah D. Angew. Chem., Int. Ed. 44 (2005) 4490
74. Bhasker G., and Rao B.V. Tetrahedron Lett. 44 (2003) 915
75. Ghosh S., Shashidar J., and Kumar Dutta S. Tetrahedron Lett. 47 (2006) 6041
76. Cha J.K., and Kim N.-S. Chem. Rev. 95 (1995) 1761
77. Cha J.K., Christ W.J., and Kishi Y. Tetrahedron Lett. 24 (1983) 3943
78. Guaragna A., D'Alonzo D., Paolella C., and Palumbo G. Tetrahedron Lett. 50 (2009) 2045
79. Takemura A., Fujiwara K., Shimawaki K., Murai A., Kawai H., and Suzuki T. Tetrahedron 61 (2005) 7392