A norbornyl route to azasugars: Stereoselective synthesis of isofagomine analogues

Tetrahedron Letters

Volumn 41, Issue 30, 2000, Pages 5747-5751

  Mehta, Goverdhan ^a   Mohal, Narinder ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

Carbohydrate mimetics; Enzyme inhibitors; Osmylation; Piperidines

Indexed keywords

FAGOMINE; ISOFAGOMINE DERIVATIVE; SUGAR ACID; UNCLASSIFIED DRUG;

ALKYLATION; AMINATION; ARTICLE; DRUG SYNTHESIS; ENZYME INHIBITION; HYDROXYLATION; METABOLIC INHIBITION; OXYGENATION; STEREOCHEMISTRY;

EID: 0034702549     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00896-0     Document Type: Article

References (20)

1. Recent Reviews: (a) Hughes, A. B.; Rudge, A. J. Nat. Prod. Rep. 1994, 135. (b) Jacob, G. S. Curr. Opin. Struct. Biol. 1995, 605. (c) Ganem, B. Acc. Chem. Res. 1996, 29, 340. (d) Bols, M. Acc. Chem. Res. 1998, 31, 1. (e) Heightman, T. D.; Vasella, A. T. Angew. Chem., Int. Ed. 1999, 38, 750. (f) Sears, P.; Wong, C.-H. ibid. 1999, 38, 2300.
2. Recent Reviews: (a) Hughes, A. B.; Rudge, A. J. Nat. Prod. Rep. 1994, 135. (b) Jacob, G. S. Curr. Opin. Struct. Biol. 1995, 605. (c) Ganem, B. Acc. Chem. Res. 1996, 29, 340. (d) Bols, M. Acc. Chem. Res. 1998, 31, 1. (e) Heightman, T. D.; Vasella, A. T. Angew. Chem., Int. Ed. 1999, 38, 750. (f) Sears, P.; Wong, C.-H. ibid. 1999, 38, 2300.
3. Recent Reviews: (a) Hughes, A. B.; Rudge, A. J. Nat. Prod. Rep. 1994, 135. (b) Jacob, G. S. Curr. Opin. Struct. Biol. 1995, 605. (c) Ganem, B. Acc. Chem. Res. 1996, 29, 340. (d) Bols, M. Acc. Chem. Res. 1998, 31, 1. (e) Heightman, T. D.; Vasella, A. T. Angew. Chem., Int. Ed. 1999, 38, 750. (f) Sears, P.; Wong, C.-H. ibid. 1999, 38, 2300.
4. Recent Reviews: (a) Hughes, A. B.; Rudge, A. J. Nat. Prod. Rep. 1994, 135. (b) Jacob, G. S. Curr. Opin. Struct. Biol. 1995, 605. (c) Ganem, B. Acc. Chem. Res. 1996, 29, 340. (d) Bols, M. Acc. Chem. Res. 1998, 31, 1. (e) Heightman, T. D.; Vasella, A. T. Angew. Chem., Int. Ed. 1999, 38, 750. (f) Sears, P.; Wong, C.-H. ibid. 1999, 38, 2300.
5. Recent Reviews: (a) Hughes, A. B.; Rudge, A. J. Nat. Prod. Rep. 1994, 135. (b) Jacob, G. S. Curr. Opin. Struct. Biol. 1995, 605. (c) Ganem, B. Acc. Chem. Res. 1996, 29, 340. (d) Bols, M. Acc. Chem. Res. 1998, 31, 1. (e) Heightman, T. D.; Vasella, A. T. Angew. Chem., Int. Ed. 1999, 38, 750. (f) Sears, P.; Wong, C.-H. ibid. 1999, 38, 2300.
6. Recent Reviews: (a) Hughes, A. B.; Rudge, A. J. Nat. Prod. Rep. 1994, 135. (b) Jacob, G. S. Curr. Opin. Struct. Biol. 1995, 605. (c) Ganem, B. Acc. Chem. Res. 1996, 29, 340. (d) Bols, M. Acc. Chem. Res. 1998, 31, 1. (e) Heightman, T. D.; Vasella, A. T. Angew. Chem., Int. Ed. 1999, 38, 750. (f) Sears, P.; Wong, C.-H. ibid. 1999, 38, 2300.
7. (a) Ikeda, K.; Takahashi, M.; Nishida, M.; Miwa, M.; Kizu, H.; Kameda, Y.; Arisawa, M.; Watson, A. A.; Nash, R. J.; Fleet, G. W. J.; Asano, N. Carbohydr. Res. 2000, 323, 73. (b) Asano, N.; Tomioka, E.; Kizu, H.; Matsui, K. ibid. 1994, 253, 235. (c) Kato, A.; Asano, A.; Kizu, H.; Matsui, K. J. Nat. Prod. 1997, 60, 312. (d) Legler, G. Adv. Carbohydr. Chem. Biochem. 1990, 48, 319.
8. (a) Ikeda, K.; Takahashi, M.; Nishida, M.; Miwa, M.; Kizu, H.; Kameda, Y.; Arisawa, M.; Watson, A. A.; Nash, R. J.; Fleet, G. W. J.; Asano, N. Carbohydr. Res. 2000, 323, 73. (b) Asano, N.; Tomioka, E.; Kizu, H.; Matsui, K. ibid. 1994, 253, 235. (c) Kato, A.; Asano, A.; Kizu, H.; Matsui, K. J. Nat. Prod. 1997, 60, 312. (d) Legler, G. Adv. Carbohydr. Chem. Biochem. 1990, 48, 319.
9. (a) Ikeda, K.; Takahashi, M.; Nishida, M.; Miwa, M.; Kizu, H.; Kameda, Y.; Arisawa, M.; Watson, A. A.; Nash, R. J.; Fleet, G. W. J.; Asano, N. Carbohydr. Res. 2000, 323, 73. (b) Asano, N.; Tomioka, E.; Kizu, H.; Matsui, K. ibid. 1994, 253, 235. (c) Kato, A.; Asano, A.; Kizu, H.; Matsui, K. J. Nat. Prod. 1997, 60, 312. (d) Legler, G. Adv. Carbohydr. Chem. Biochem. 1990, 48, 319.
10. (a) Ikeda, K.; Takahashi, M.; Nishida, M.; Miwa, M.; Kizu, H.; Kameda, Y.; Arisawa, M.; Watson, A. A.; Nash, R. J.; Fleet, G. W. J.; Asano, N. Carbohydr. Res. 2000, 323, 73. (b) Asano, N.; Tomioka, E.; Kizu, H.; Matsui, K. ibid. 1994, 253, 235. (c) Kato, A.; Asano, A.; Kizu, H.; Matsui, K. J. Nat. Prod. 1997, 60, 312. (d) Legler, G. Adv. Carbohydr. Chem. Biochem. 1990, 48, 319.
11. (a) Ichikawa, Y.; Igarashi, Y., Tetrahedron Lett. 1995, 36, 4585. (b) Ichikawa, Y.; Igarashi, Y.; Ichikawa, M.; Suhara, Y. J. Am. Chem. Soc. 1998, 120, 3007. (c) Jespersen, T. M.; Dong, W.; Sierks, M. R.; Skrydsurp, T.; Lundt, I.; Bols, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1778. (d) Hansen, A.; Tagmose, T. M.; Bols, M. Chem. Commun. 1996, 2649. (e) Ernholt, B. V.; Thomson, I. B.; Jensen, K.; Bols, M. Synlett 1999, 6, 701. (f) Hensen, S. U.; Bols, M. J. Chem. Soc., Perkin Trans. 1 2000, 911 and references cited therein.
12. (a) Ichikawa, Y.; Igarashi, Y., Tetrahedron Lett. 1995, 36, 4585. (b) Ichikawa, Y.; Igarashi, Y.; Ichikawa, M.; Suhara, Y. J. Am. Chem. Soc. 1998, 120, 3007. (c) Jespersen, T. M.; Dong, W.; Sierks, M. R.; Skrydsurp, T.; Lundt, I.; Bols, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1778. (d) Hansen, A.; Tagmose, T. M.; Bols, M. Chem. Commun. 1996, 2649. (e) Ernholt, B. V.; Thomson, I. B.; Jensen, K.; Bols, M. Synlett 1999, 6, 701. (f) Hensen, S. U.; Bols, M. J. Chem. Soc., Perkin Trans. 1 2000, 911 and references cited therein.
13. (a) Ichikawa, Y.; Igarashi, Y., Tetrahedron Lett. 1995, 36, 4585. (b) Ichikawa, Y.; Igarashi, Y.; Ichikawa, M.; Suhara, Y. J. Am. Chem. Soc. 1998, 120, 3007. (c) Jespersen, T. M.; Dong, W.; Sierks, M. R.; Skrydsurp, T.; Lundt, I.; Bols, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1778. (d) Hansen, A.; Tagmose, T. M.; Bols, M. Chem. Commun. 1996, 2649. (e) Ernholt, B. V.; Thomson, I. B.; Jensen, K.; Bols, M. Synlett 1999, 6, 701. (f) Hensen, S. U.; Bols, M. J. Chem. Soc., Perkin Trans. 1 2000, 911 and references cited therein.
14. (a) Ichikawa, Y.; Igarashi, Y., Tetrahedron Lett. 1995, 36, 4585. (b) Ichikawa, Y.; Igarashi, Y.; Ichikawa, M.; Suhara, Y. J. Am. Chem. Soc. 1998, 120, 3007. (c) Jespersen, T. M.; Dong, W.; Sierks, M. R.; Skrydsurp, T.; Lundt, I.; Bols, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1778. (d) Hansen, A.; Tagmose, T. M.; Bols, M. Chem. Commun. 1996, 2649. (e) Ernholt, B. V.; Thomson, I. B.; Jensen, K.; Bols, M. Synlett 1999, 6, 701. (f) Hensen, S. U.; Bols, M. J. Chem. Soc., Perkin Trans. 1 2000, 911 and references cited therein.
15. (a) Ichikawa, Y.; Igarashi, Y., Tetrahedron Lett. 1995, 36, 4585. (b) Ichikawa, Y.; Igarashi, Y.; Ichikawa, M.; Suhara, Y. J. Am. Chem. Soc. 1998, 120, 3007. (c) Jespersen, T. M.; Dong, W.; Sierks, M. R.; Skrydsurp, T.; Lundt, I.; Bols, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1778. (d) Hansen, A.; Tagmose, T. M.; Bols, M. Chem. Commun. 1996, 2649. (e) Ernholt, B. V.; Thomson, I. B.; Jensen, K.; Bols, M. Synlett 1999, 6, 701. (f) Hensen, S. U.; Bols, M. J. Chem. Soc., Perkin Trans. 1 2000, 911 and references cited therein.
16. (a) Ichikawa, Y.; Igarashi, Y., Tetrahedron Lett. 1995, 36, 4585. (b) Ichikawa, Y.; Igarashi, Y.; Ichikawa, M.; Suhara, Y. J. Am. Chem. Soc. 1998, 120, 3007. (c) Jespersen, T. M.; Dong, W.; Sierks, M. R.; Skrydsurp, T.; Lundt, I.; Bols, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1778. (d) Hansen, A.; Tagmose, T. M.; Bols, M. Chem. Commun. 1996, 2649. (e) Ernholt, B. V.; Thomson, I. B.; Jensen, K.; Bols, M. Synlett 1999, 6, 701. (f) Hensen, S. U.; Bols, M. J. Chem. Soc., Perkin Trans. 1 2000, 911 and references cited therein.
17. Mehta, G.; Mohal, N. Tetrahedron Lett. 1999, 40, 5791.
18. 3).
19. Baxter, E. W.; Reitz, A. B. J. Org. Chem. 1994, 59, 3175.
20. Butters, T. D.; van den Broek, L. A. G. M.; Fleet, G. W. J.; Krulle, T. M.; Wormald, M. R.; Dwek, R. A.; Platt, F. M. Tetrahedron: Asymmetry 2000, 11, 113.