A potentially divergent and rapid route to analogues of deoxycyclitols, pentopyranoses, 6-deoxyhexoses, and hexoses

Organic Letters

Volumn 6, Issue 23, 2004, Pages 4269-4272

  Audouard, Christophe ^a   Fawcett, John ^a   Griffith, Gerry A ^a   Kérourédan, Erwan ^a   Miah, Afjal ^a   Percy, Jonathan M ^a   Yang, Hongli ^a  

^a UNIVERSITY OF LEICESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ACROLEIN; CINNAMALDEHYDE DERIVATIVE; HEXOSE; OXYGEN; PYRAN DERIVATIVE;

ADDITION REACTION; ALLYLATION; ARTICLE; CHEMICAL REACTION; FLUORINATION; SYNTHESIS;

EID: 9444281976     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0482902     Document Type: Article

References (46)

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19. For related species, see (c) Lampe, D.; Liu, C.; Mahon, M. F.; Potter, B. V. L. J. Chem. Soc., Perkin Trans. 1 1996, 1717. (d) Kozikowski, A. P.; Fauq, A. H.; Wilcox, R. A.; Nahorski, S. R. Bioorg. Med. Chem. Lett. 1995, 5, 1295. (e) Rich, R. H.; Lawrence, B. M.; Bartlett, P. A. J. Org. Chem. 1994, 59, 693. (f) Jiang, S.; Singh, G.; Boam, D. J.; Coggins, J. R. Tetrahedron: Asymmetry. 1999, 10, 4087. (g) Eguchi, T.; Sasaki, S.; Huang, Z.; Kakinuma, K. J. Org. Chem. 2002, 67, 3979. For a recent review fluorinated cyclitol analogues as probes, see: (h) Schedler, D. J. A.; Baker, D. C. Carbohydr. Res. 2004, 339, 1585.
20. For related species, see (c) Lampe, D.; Liu, C.; Mahon, M. F.; Potter, B. V. L. J. Chem. Soc., Perkin Trans. 1 1996, 1717. (d) Kozikowski, A. P.; Fauq, A. H.; Wilcox, R. A.; Nahorski, S. R. Bioorg. Med. Chem. Lett. 1995, 5, 1295. (e) Rich, R. H.; Lawrence, B. M.; Bartlett, P. A. J. Org. Chem. 1994, 59, 693. (f) Jiang, S.; Singh, G.; Boam, D. J.; Coggins, J. R. Tetrahedron: Asymmetry. 1999, 10, 4087. (g) Eguchi, T.; Sasaki, S.; Huang, Z.; Kakinuma, K. J. Org. Chem. 2002, 67, 3979. For a recent review fluorinated cyclitol analogues as probes, see: (h) Schedler, D. J. A.; Baker, D. C. Carbohydr. Res. 2004, 339, 1585.
21. For related species, see (c) Lampe, D.; Liu, C.; Mahon, M. F.; Potter, B. V. L. J. Chem. Soc., Perkin Trans. 1 1996, 1717. (d) Kozikowski, A. P.; Fauq, A. H.; Wilcox, R. A.; Nahorski, S. R. Bioorg. Med. Chem. Lett. 1995, 5, 1295. (e) Rich, R. H.; Lawrence, B. M.; Bartlett, P. A. J. Org. Chem. 1994, 59, 693. (f) Jiang, S.; Singh, G.; Boam, D. J.; Coggins, J. R. Tetrahedron: Asymmetry. 1999, 10, 4087. (g) Eguchi, T.; Sasaki, S.; Huang, Z.; Kakinuma, K. J. Org. Chem. 2002, 67, 3979. For a recent review fluorinated cyclitol analogues as probes, see: (h) Schedler, D. J. A.; Baker, D. C. Carbohydr. Res. 2004, 339, 1585.
22. For related species, see (c) Lampe, D.; Liu, C.; Mahon, M. F.; Potter, B. V. L. J. Chem. Soc., Perkin Trans. 1 1996, 1717. (d) Kozikowski, A. P.; Fauq, A. H.; Wilcox, R. A.; Nahorski, S. R. Bioorg. Med. Chem. Lett. 1995, 5, 1295. (e) Rich, R. H.; Lawrence, B. M.; Bartlett, P. A. J. Org. Chem. 1994, 59, 693. (f) Jiang, S.; Singh, G.; Boam, D. J.; Coggins, J. R. Tetrahedron: Asymmetry. 1999, 10, 4087. (g) Eguchi, T.; Sasaki, S.; Huang, Z.; Kakinuma, K. J. Org. Chem. 2002, 67, 3979. For a recent review fluorinated cyclitol analogues as probes, see: (h) Schedler, D. J. A.; Baker, D. C. Carbohydr. Res. 2004, 339, 1585.
23. For related species, see (c) Lampe, D.; Liu, C.; Mahon, M. F.; Potter, B. V. L. J. Chem. Soc., Perkin Trans. 1 1996, 1717. (d) Kozikowski, A. P.; Fauq, A. H.; Wilcox, R. A.; Nahorski, S. R. Bioorg. Med. Chem. Lett. 1995, 5, 1295. (e) Rich, R. H.; Lawrence, B. M.; Bartlett, P. A. J. Org. Chem. 1994, 59, 693. (f) Jiang, S.; Singh, G.; Boam, D. J.; Coggins, J. R. Tetrahedron: Asymmetry. 1999, 10, 4087. (g) Eguchi, T.; Sasaki, S.; Huang, Z.; Kakinuma, K. J. Org. Chem. 2002, 67, 3979. For a recent review fluorinated cyclitol analogues as probes, see: (h) Schedler, D. J. A.; Baker, D. C. Carbohydr. Res. 2004, 339, 1585.
24. For related species, see (c) Lampe, D.; Liu, C.; Mahon, M. F.; Potter, B. V. L. J. Chem. Soc., Perkin Trans. 1 1996, 1717. (d) Kozikowski, A. P.; Fauq, A. H.; Wilcox, R. A.; Nahorski, S. R. Bioorg. Med. Chem. Lett. 1995, 5, 1295. (e) Rich, R. H.; Lawrence, B. M.; Bartlett, P. A. J. Org. Chem. 1994, 59, 693. (f) Jiang, S.; Singh, G.; Boam, D. J.; Coggins, J. R. Tetrahedron: Asymmetry. 1999, 10, 4087. (g) Eguchi, T.; Sasaki, S.; Huang, Z.; Kakinuma, K. J. Org. Chem. 2002, 67, 3979. For a recent review fluorinated cyclitol analogues as probes, see: (h) Schedler, D. J. A.; Baker, D. C. Carbohydr. Res. 2004, 339, 1585.
25. Scholl, M.; Trnka, T. M.; Morgan, J. P.; Grubbs, R. H. Tetrahedron Lett. 1999, 40, 2247.
26. For strong direct precedents, see: (a) Ackermann, L.; El Tom, D.; Furstner, A. Tetrahedron 2000, 56, 2195. (b) Hyldtoft, L.; Madsen, R. J. Am. Chem. Soc. 2000, 122, 8444. (c) Conrad, R. M.; Grogan, M. J.; Bertozzi, C. R. Org. Lett. 2002, 4, 1359. (d) Heo, J. N.; Holson, E. B.; Roush, W. R. Org. Lett. 2003, 5, 1697.
27. For strong direct precedents, see: (a) Ackermann, L.; El Tom, D.; Furstner, A. Tetrahedron 2000, 56, 2195. (b) Hyldtoft, L.; Madsen, R. J. Am. Chem. Soc. 2000, 122, 8444. (c) Conrad, R. M.; Grogan, M. J.; Bertozzi, C. R. Org. Lett. 2002, 4, 1359. (d) Heo, J. N.; Holson, E. B.; Roush, W. R. Org. Lett. 2003, 5, 1697.
28. For strong direct precedents, see: (a) Ackermann, L.; El Tom, D.; Furstner, A. Tetrahedron 2000, 56, 2195. (b) Hyldtoft, L.; Madsen, R. J. Am. Chem. Soc. 2000, 122, 8444. (c) Conrad, R. M.; Grogan, M. J.; Bertozzi, C. R. Org. Lett. 2002, 4, 1359. (d) Heo, J. N.; Holson, E. B.; Roush, W. R. Org. Lett. 2003, 5, 1697.
29. For strong direct precedents, see: (a) Ackermann, L.; El Tom, D.; Furstner, A. Tetrahedron 2000, 56, 2195. (b) Hyldtoft, L.; Madsen, R. J. Am. Chem. Soc. 2000, 122, 8444. (c) Conrad, R. M.; Grogan, M. J.; Bertozzi, C. R. Org. Lett. 2002, 4, 1359. (d) Heo, J. N.; Holson, E. B.; Roush, W. R. Org. Lett. 2003, 5, 1697.
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31. For other examples of the dehydrofluorination/metalation approach, see: (b) Nakai, T.; Tanaka, K.; Ishihawa, N. Chem. Lett. 1976, 1263. (c) Ichikawa, J.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1989, 30, 6379. (d) Patel, S. T.; Percy, J. M.; Wilkes, R. D. Tetrahedron 1995, 51, 9201. (e) Howarth, J. A.; Owton, W. M.; Percy, J. M.; Rock, M. H. Tetrahedron 1995, 51, 10289. (f) Harrington, P. E.; Tius, M. A. J. Org. Chem. 1999, 64, 4025. (g) See Cox, L. R.; DeBoos, G. A.; Fullbrook, J. J.; Percy, J. M.; Spencer, N. S.; Tolley, M. Org. Lett. 2003, 5, 337 for applications of dehydrofluorination/metalation methodology in asymmetric synthesis.
32. For other examples of the dehydrofluorination/metalation approach, see: (b) Nakai, T.; Tanaka, K.; Ishihawa, N. Chem. Lett. 1976, 1263. (c) Ichikawa, J.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1989, 30, 6379. (d) Patel, S. T.; Percy, J. M.; Wilkes, R. D. Tetrahedron 1995, 51, 9201. (e) Howarth, J. A.; Owton, W. M.; Percy, J. M.; Rock, M. H. Tetrahedron 1995, 51, 10289. (f) Harrington, P. E.; Tius, M. A. J. Org. Chem. 1999, 64, 4025. (g) See Cox, L. R.; DeBoos, G. A.; Fullbrook, J. J.; Percy, J. M.; Spencer, N. S.; Tolley, M. Org. Lett. 2003, 5, 337 for applications of dehydrofluorination/metalation methodology in asymmetric synthesis.
33. For other examples of the dehydrofluorination/metalation approach, see: (b) Nakai, T.; Tanaka, K.; Ishihawa, N. Chem. Lett. 1976, 1263. (c) Ichikawa, J.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1989, 30, 6379. (d) Patel, S. T.; Percy, J. M.; Wilkes, R. D. Tetrahedron 1995, 51, 9201. (e) Howarth, J. A.; Owton, W. M.; Percy, J. M.; Rock, M. H. Tetrahedron 1995, 51, 10289. (f) Harrington, P. E.; Tius, M. A. J. Org. Chem. 1999, 64, 4025. (g) See Cox, L. R.; DeBoos, G. A.; Fullbrook, J. J.; Percy, J. M.; Spencer, N. S.; Tolley, M. Org. Lett. 2003, 5, 337 for applications of dehydrofluorination/metalation methodology in asymmetric synthesis.
34. For other examples of the dehydrofluorination/metalation approach, see: (b) Nakai, T.; Tanaka, K.; Ishihawa, N. Chem. Lett. 1976, 1263. (c) Ichikawa, J.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1989, 30, 6379. (d) Patel, S. T.; Percy, J. M.; Wilkes, R. D. Tetrahedron 1995, 51, 9201. (e) Howarth, J. A.; Owton, W. M.; Percy, J. M.; Rock, M. H. Tetrahedron 1995, 51, 10289. (f) Harrington, P. E.; Tius, M. A. J. Org. Chem. 1999, 64, 4025. (g) See Cox, L. R.; DeBoos, G. A.; Fullbrook, J. J.; Percy, J. M.; Spencer, N. S.; Tolley, M. Org. Lett. 2003, 5, 337 for applications of dehydrofluorination/metalation methodology in asymmetric synthesis.
35. For other examples of the dehydrofluorination/metalation approach, see: (b) Nakai, T.; Tanaka, K.; Ishihawa, N. Chem. Lett. 1976, 1263. (c) Ichikawa, J.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1989, 30, 6379. (d) Patel, S. T.; Percy, J. M.; Wilkes, R. D. Tetrahedron 1995, 51, 9201. (e) Howarth, J. A.; Owton, W. M.; Percy, J. M.; Rock, M. H. Tetrahedron 1995, 51, 10289. (f) Harrington, P. E.; Tius, M. A. J. Org. Chem. 1999, 64, 4025. (g) See Cox, L. R.; DeBoos, G. A.; Fullbrook, J. J.; Percy, J. M.; Spencer, N. S.; Tolley, M. Org. Lett. 2003, 5, 337 for applications of dehydrofluorination/metalation methodology in asymmetric synthesis.
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