A norbornyl route to azasugars: A new synthesis of deoxynojirimycin analogues

Tetrahedron Letters

Volumn 41, Issue 30, 2000, Pages 5741-5745

  Mehta, Goverdhan ^a   Mohal, Narinder ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

Azasugars; Glycosidase inhibitors; Osmylation; Reductive amination

Indexed keywords

DEOXYNOJIRIMYCIN DERIVATIVE; NOJIRIMYCIN; SUGAR ACID; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; COMPETITIVE INHIBITION; DERIVATIZATION; DRUG SYNTHESIS; ENZYME INHIBITION; HYDROXYLATION; STEREOCHEMISTRY;

EID: 0034702515     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00895-9     Document Type: Article

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21. For the isolation and enzyme inhibitory activity of the potent DNJ, deoxygalactostatin, see: Miyake, Y.; Ebata, M. J. J Antibiotics 1987, 40, 122. For the leading references towards the synthesis of deoxygalactostatin and analogues, see: (a) Paulson, H.; Hayauchi, Y.; Sinnwell, V. Chem. Ber. 1980, 113, 2601. (b) Bernotas, R.; Pezzone, M. A.; Ganem, B. Carbohydr. Res. 1987, 167, 305. (c) Furneaux, R. H.; Tyler, P. C.; Whitehouse, L. A. Tetrahedron Lett. 1993, 34, 3609. (d) Chida, N.; Tanikawa, T.; Tobe, T.; Ogawa, S. Chem. Commun. 1994, 1247. (e) Johnson, C. R.; Golebiowski, A.; Sundram, H.; Miller, M. W.; Dwaihy, R. L. Tetrahedron Lett. 1995, 36, 653. (f) Barili, P. L.; Berti, G.; Catelani, G.; D'Andrea, F.; De Rensis, F.; Puccioni, L. Tetrahedron 1997, 53, 3407. (g) Shilvock, J. V.; Fleet, G. W. J. Synlett 1998, 554. (h) Asano, K.; Hakogi, T.; Iwana, S.; Katumura, S. Chem. Commun. 1999, 41. (i) Uriel, C.; Santoyo-Gonazaleaz, F. Synlett 1999, 593. (j) Ruiz, M.; Ruanova, T. M.; Ojea, V.; Quintela, J. M. Tetrahedron Lett. 1999, 40, 2021.
22. For the isolation and enzyme inhibitory activity of the potent DNJ, deoxygalactostatin, see: Miyake, Y.; Ebata, M. J. J Antibiotics 1987, 40, 122. For the leading references towards the synthesis of deoxygalactostatin and analogues, see: (a) Paulson, H.; Hayauchi, Y.; Sinnwell, V. Chem. Ber. 1980, 113, 2601. (b) Bernotas, R.; Pezzone, M. A.; Ganem, B. Carbohydr. Res. 1987, 167, 305. (c) Furneaux, R. H.; Tyler, P. C.; Whitehouse, L. A. Tetrahedron Lett. 1993, 34, 3609. (d) Chida, N.; Tanikawa, T.; Tobe, T.; Ogawa, S. Chem. Commun. 1994, 1247. (e) Johnson, C. R.; Golebiowski, A.; Sundram, H.; Miller, M. W.; Dwaihy, R. L. Tetrahedron Lett. 1995, 36, 653. (f) Barili, P. L.; Berti, G.; Catelani, G.; D'Andrea, F.; De Rensis, F.; Puccioni, L. Tetrahedron 1997, 53, 3407. (g) Shilvock, J. V.; Fleet, G. W. J. Synlett 1998, 554. (h) Asano, K.; Hakogi, T.; Iwana, S.; Katumura, S. Chem. Commun. 1999, 41. (i) Uriel, C.; Santoyo-Gonazaleaz, F. Synlett 1999, 593. (j) Ruiz, M.; Ruanova, T. M.; Ojea, V.; Quintela, J. M. Tetrahedron Lett. 1999, 40, 2021.
23. For the isolation and enzyme inhibitory activity of the potent DNJ, deoxygalactostatin, see: Miyake, Y.; Ebata, M. J. J Antibiotics 1987, 40, 122. For the leading references towards the synthesis of deoxygalactostatin and analogues, see: (a) Paulson, H.; Hayauchi, Y.; Sinnwell, V. Chem. Ber. 1980, 113, 2601. (b) Bernotas, R.; Pezzone, M. A.; Ganem, B. Carbohydr. Res. 1987, 167, 305. (c) Furneaux, R. H.; Tyler, P. C.; Whitehouse, L. A. Tetrahedron Lett. 1993, 34, 3609. (d) Chida, N.; Tanikawa, T.; Tobe, T.; Ogawa, S. Chem. Commun. 1994, 1247. (e) Johnson, C. R.; Golebiowski, A.; Sundram, H.; Miller, M. W.; Dwaihy, R. L. Tetrahedron Lett. 1995, 36, 653. (f) Barili, P. L.; Berti, G.; Catelani, G.; D'Andrea, F.; De Rensis, F.; Puccioni, L. Tetrahedron 1997, 53, 3407. (g) Shilvock, J. V.; Fleet, G. W. J. Synlett 1998, 554. (h) Asano, K.; Hakogi, T.; Iwana, S.; Katumura, S. Chem. Commun. 1999, 41. (i) Uriel, C.; Santoyo-Gonazaleaz, F. Synlett 1999, 593. (j) Ruiz, M.; Ruanova, T. M.; Ojea, V.; Quintela, J. M. Tetrahedron Lett. 1999, 40, 2021.
24. For the isolation and enzyme inhibitory activity of the potent DNJ, deoxygalactostatin, see: Miyake, Y.; Ebata, M. J. J Antibiotics 1987, 40, 122. For the leading references towards the synthesis of deoxygalactostatin and analogues, see: (a) Paulson, H.; Hayauchi, Y.; Sinnwell, V. Chem. Ber. 1980, 113, 2601. (b) Bernotas, R.; Pezzone, M. A.; Ganem, B. Carbohydr. Res. 1987, 167, 305. (c) Furneaux, R. H.; Tyler, P. C.; Whitehouse, L. A. Tetrahedron Lett. 1993, 34, 3609. (d) Chida, N.; Tanikawa, T.; Tobe, T.; Ogawa, S. Chem. Commun. 1994, 1247. (e) Johnson, C. R.; Golebiowski, A.; Sundram, H.; Miller, M. W.; Dwaihy, R. L. Tetrahedron Lett. 1995, 36, 653. (f) Barili, P. L.; Berti, G.; Catelani, G.; D'Andrea, F.; De Rensis, F.; Puccioni, L. Tetrahedron 1997, 53, 3407. (g) Shilvock, J. V.; Fleet, G. W. J. Synlett 1998, 554. (h) Asano, K.; Hakogi, T.; Iwana, S.; Katumura, S. Chem. Commun. 1999, 41. (i) Uriel, C.; Santoyo-Gonazaleaz, F. Synlett 1999, 593. (j) Ruiz, M.; Ruanova, T. M.; Ojea, V.; Quintela, J. M. Tetrahedron Lett. 1999, 40, 2021.
25. For the isolation and enzyme inhibitory activity of the potent DNJ, deoxygalactostatin, see: Miyake, Y.; Ebata, M. J. J Antibiotics 1987, 40, 122. For the leading references towards the synthesis of deoxygalactostatin and analogues, see: (a) Paulson, H.; Hayauchi, Y.; Sinnwell, V. Chem. Ber. 1980, 113, 2601. (b) Bernotas, R.; Pezzone, M. A.; Ganem, B. Carbohydr. Res. 1987, 167, 305. (c) Furneaux, R. H.; Tyler, P. C.; Whitehouse, L. A. Tetrahedron Lett. 1993, 34, 3609. (d) Chida, N.; Tanikawa, T.; Tobe, T.; Ogawa, S. Chem. Commun. 1994, 1247. (e) Johnson, C. R.; Golebiowski, A.; Sundram, H.; Miller, M. W.; Dwaihy, R. L. Tetrahedron Lett. 1995, 36, 653. (f) Barili, P. L.; Berti, G.; Catelani, G.; D'Andrea, F.; De Rensis, F.; Puccioni, L. Tetrahedron 1997, 53, 3407. (g) Shilvock, J. V.; Fleet, G. W. J. Synlett 1998, 554. (h) Asano, K.; Hakogi, T.; Iwana, S.; Katumura, S. Chem. Commun. 1999, 41. (i) Uriel, C.; Santoyo-Gonazaleaz, F. Synlett 1999, 593. (j) Ruiz, M.; Ruanova, T. M.; Ojea, V.; Quintela, J. M. Tetrahedron Lett. 1999, 40, 2021.
26. For the isolation and enzyme inhibitory activity of the potent DNJ, deoxygalactostatin, see: Miyake, Y.; Ebata, M. J. J Antibiotics 1987, 40, 122. For the leading references towards the synthesis of deoxygalactostatin and analogues, see: (a) Paulson, H.; Hayauchi, Y.; Sinnwell, V. Chem. Ber. 1980, 113, 2601. (b) Bernotas, R.; Pezzone, M. A.; Ganem, B. Carbohydr. Res. 1987, 167, 305. (c) Furneaux, R. H.; Tyler, P. C.; Whitehouse, L. A. Tetrahedron Lett. 1993, 34, 3609. (d) Chida, N.; Tanikawa, T.; Tobe, T.; Ogawa, S. Chem. Commun. 1994, 1247. (e) Johnson, C. R.; Golebiowski, A.; Sundram, H.; Miller, M. W.; Dwaihy, R. L. Tetrahedron Lett. 1995, 36, 653. (f) Barili, P. L.; Berti, G.; Catelani, G.; D'Andrea, F.; De Rensis, F.; Puccioni, L. Tetrahedron 1997, 53, 3407. (g) Shilvock, J. V.; Fleet, G. W. J. Synlett 1998, 554. (h) Asano, K.; Hakogi, T.; Iwana, S.; Katumura, S. Chem. Commun. 1999, 41. (i) Uriel, C.; Santoyo-Gonazaleaz, F. Synlett 1999, 593. (j) Ruiz, M.; Ruanova, T. M.; Ojea, V.; Quintela, J. M. Tetrahedron Lett. 1999, 40, 2021.
27. For the isolation and enzyme inhibitory activity of the potent DNJ, deoxygalactostatin, see: Miyake, Y.; Ebata, M. J. J Antibiotics 1987, 40, 122. For the leading references towards the synthesis of deoxygalactostatin and analogues, see: (a) Paulson, H.; Hayauchi, Y.; Sinnwell, V. Chem. Ber. 1980, 113, 2601. (b) Bernotas, R.; Pezzone, M. A.; Ganem, B. Carbohydr. Res. 1987, 167, 305. (c) Furneaux, R. H.; Tyler, P. C.; Whitehouse, L. A. Tetrahedron Lett. 1993, 34, 3609. (d) Chida, N.; Tanikawa, T.; Tobe, T.; Ogawa, S. Chem. Commun. 1994, 1247. (e) Johnson, C. R.; Golebiowski, A.; Sundram, H.; Miller, M. W.; Dwaihy, R. L. Tetrahedron Lett. 1995, 36, 653. (f) Barili, P. L.; Berti, G.; Catelani, G.; D'Andrea, F.; De Rensis, F.; Puccioni, L. Tetrahedron 1997, 53, 3407. (g) Shilvock, J. V.; Fleet, G. W. J. Synlett 1998, 554. (h) Asano, K.; Hakogi, T.; Iwana, S.; Katumura, S. Chem. Commun. 1999, 41. (i) Uriel, C.; Santoyo-Gonazaleaz, F. Synlett 1999, 593. (j) Ruiz, M.; Ruanova, T. M.; Ojea, V.; Quintela, J. M. Tetrahedron Lett. 1999, 40, 2021.
28. For the isolation and enzyme inhibitory activity of the potent DNJ, deoxygalactostatin, see: Miyake, Y.; Ebata, M. J. J Antibiotics 1987, 40, 122. For the leading references towards the synthesis of deoxygalactostatin and analogues, see: (a) Paulson, H.; Hayauchi, Y.; Sinnwell, V. Chem. Ber. 1980, 113, 2601. (b) Bernotas, R.; Pezzone, M. A.; Ganem, B. Carbohydr. Res. 1987, 167, 305. (c) Furneaux, R. H.; Tyler, P. C.; Whitehouse, L. A. Tetrahedron Lett. 1993, 34, 3609. (d) Chida, N.; Tanikawa, T.; Tobe, T.; Ogawa, S. Chem. Commun. 1994, 1247. (e) Johnson, C. R.; Golebiowski, A.; Sundram, H.; Miller, M. W.; Dwaihy, R. L. Tetrahedron Lett. 1995, 36, 653. (f) Barili, P. L.; Berti, G.; Catelani, G.; D'Andrea, F.; De Rensis, F.; Puccioni, L. Tetrahedron 1997, 53, 3407. (g) Shilvock, J. V.; Fleet, G. W. J. Synlett 1998, 554. (h) Asano, K.; Hakogi, T.; Iwana, S.; Katumura, S. Chem. Commun. 1999, 41. (i) Uriel, C.; Santoyo-Gonazaleaz, F. Synlett 1999, 593. (j) Ruiz, M.; Ruanova, T. M.; Ojea, V.; Quintela, J. M. Tetrahedron Lett. 1999, 40, 2021.
29. 2).