Fragmentation of Carbohydrate Anomeric Alkoxy Radicals. A New General Method for the Synthesis of Alduronic Acid Lactones

Journal of Organic Chemistry

Volumn 63, Issue 7, 1998, Pages 2099-2109

  Francisco, Cosme G ^a   Martín, Concepción González ^a   Suárez, Ernesto ^a  

^a INSTITUTO DE PRODUCTOS NATURALES Y AGROBIOLOGÍA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000171763     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971323p     Document Type: Article

References (63)

1. Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press: New York, 1986.
2. (b) Surzur, J.-M.; Bertrand, M. P. Pure Appl. Chem. 1988, 60, 1659.
3. (c) Clive, D. L. Pure Appl. Chem. 1988, 60, 1645.
4. (d) Neumann, W. P. Synthesis 1987, 665,
5. (e) Stork, G.; Reynolds, M. E. J. Am. Chem. Soc. 1988, 110, 6911.
6. Ho, T.-L. Tandem Organic Reactions; Wiley-Interscience: New York, 1992.
7. (b) Bunce, R. A. Tetrahedron 1995, 51, 13103.
8. Hanessian, S. Total Synthesis of Natural Products. The Chiron Approach; Pergamon Press: Oxford, 1983. Inch, T. D. Tetrahedron 1984, 40, 3161
9. Hanessian, S. Total Synthesis of Natural Products. The Chiron Approach; Pergamon Press: Oxford, 1983. Inch, T. D. Tetrahedron 1984, 40, 3161
10. Freire, R.; Marrero, J, J.; Rodríguez, M. S.; Suárez, E. Tetrahedron Lett. 1986, 27, 383.
11. (b) Arencibia, M. T.; Freire, R.; Perales, A.; Rodríguez, M. S.; Suárez, E. J. Chem. Soc., Perkin Trans. 1 1991, 3349.
12. (a) Armas, P.; Francisco, C. G.; Suárez, E. J. Am. Chem. Soc. 1993, 115, 8865.
13. (b) Armas, P.; Francisco, C. G.; Suárez, E. Tetrahedron Lett. 1993, 34, 7331.
14. For late reviews on iodine hypervalent reagents see: (a) Prakash, O.; Saini, N.; Sharma, P. K. Heterocycles 1994, 38, 409. (b) Varvoglis, A. Tetrahedron 1997, 53, 1179. Varvoglis, A. Hypervalent Iodine in Organic Synthesis; Academic Press: San Diego, 1997 and references therein.
15. For late reviews on iodine hypervalent reagents see: (a) Prakash, O.; Saini, N.; Sharma, P. K. Heterocycles 1994, 38, 409. (b) Varvoglis, A. Tetrahedron 1997, 53, 1179. Varvoglis, A. Hypervalent Iodine in Organic Synthesis; Academic Press: San Diego, 1997 and references therein.
16. For late reviews on iodine hypervalent reagents see: (a) Prakash, O.; Saini, N.; Sharma, P. K. Heterocycles 1994, 38, 409. (b) Varvoglis, A. Tetrahedron 1997, 53, 1179. Varvoglis, A. Hypervalent Iodine in Organic Synthesis; Academic Press: San Diego, 1997 and references therein.
17. For preliminary report see: Francisco, C. G.; Gonzalez, C. C.; Suárez, E. Tetrahedron Lett. 1996, 37, 1687.
18. (a) Agrofoglio, L.; Suhas, E.; Farese, A.; Condom, R.; Challand, S. R.; Earl, R. A.; Guedj, R. Tetrahedron 1994, 50, 10611.
19. (b) Jenkins, G. N.; Turner, N. J. Chem. Soc. Rev. 1995, 24, 169.
20. (c) Huryn, D. M.; Okabe, M. Chem. Rev. 1992, 92, 1745.
21. (a) Belleau, B. J. Am. Chem. Soc. 1951, 73, 5441.
22. (b) Fujimoto, G. I. J. Am. Chem. Soc. 1951, 73, 1856.
23. (a) Borcherding, D. R.; Scholtz, S. A.; Borchardt, R. T. J. Org. Chem. 1987, 52, 5457.
24. (b) Wolfe, M. S.; Borcherding, D. R.; Borchardt, R. T. Tetrahedron Lett. 1989, 30, 1453.
25. (c) Ali, S. M.; Ramesh, K.; Borchardt, R. T. Tetrahedron Lett. 1990, 31, 1509.
26. For other methods of synthesis of 2,3-dihydroxy-4-cyclopentenones see: (d) Armstrong, A.; Hayter, B. R. Tetrahedron: Asymmetry 1997, 8, 1677. (e) Sundermann, B.; Scharf, H.-D. Tetrahedron: Asymmetry 1996, 7, 1995. (f) Johnson, C. R.; Esker, J. L.; Van Zandt, M. C. J. Org. Chem. 1994, 59, 5854. (g) Beer, D.; Meuwly, R.; Vasella, A. Helv. Chim. Acta 1982, 65, 2570. (h) Bélanger, P.; Prasit, P. Tetrahedron Lett. 1988, 29, 5521. (i) Bestmann, H. J.; Moenius, T. Angew. Chem., Int. Ed. Engl. 1986, 25, 994. (j) Deardorft, D. R.; Shambayati, S.; Myles, D. C.; Heerding, D. J. Org. Chem. 1988, 53, 3614. (k) Hudlicky, T.; Luna, H. Barbieri, G.; Kwart, L. D. J. Am. Chem. Soc. 1988, 110, 4735.
27. For other methods of synthesis of 2,3-dihydroxy-4-cyclopentenones see: (d) Armstrong, A.; Hayter, B. R. Tetrahedron: Asymmetry 1997, 8, 1677. (e) Sundermann, B.; Scharf, H.-D. Tetrahedron: Asymmetry 1996, 7, 1995. (f) Johnson, C. R.; Esker, J. L.; Van Zandt, M. C. J. Org. Chem. 1994, 59, 5854. (g) Beer, D.; Meuwly, R.; Vasella, A. Helv. Chim. Acta 1982, 65, 2570. (h) Bélanger, P.; Prasit, P. Tetrahedron Lett. 1988, 29, 5521. (i) Bestmann, H. J.; Moenius, T. Angew. Chem., Int. Ed. Engl. 1986, 25, 994. (j) Deardorft, D. R.; Shambayati, S.; Myles, D. C.; Heerding, D. J. Org. Chem. 1988, 53, 3614. (k) Hudlicky, T.; Luna, H. Barbieri, G.; Kwart, L. D. J. Am. Chem. Soc. 1988, 110, 4735.
28. For other methods of synthesis of 2,3-dihydroxy-4-cyclopentenones see: (d) Armstrong, A.; Hayter, B. R. Tetrahedron: Asymmetry 1997, 8, 1677. (e) Sundermann, B.; Scharf, H.-D. Tetrahedron: Asymmetry 1996, 7, 1995. (f) Johnson, C. R.; Esker, J. L.; Van Zandt, M. C. J. Org. Chem. 1994, 59, 5854. (g) Beer, D.; Meuwly, R.; Vasella, A. Helv. Chim. Acta 1982, 65, 2570. (h) Bélanger, P.; Prasit, P. Tetrahedron Lett. 1988, 29, 5521. (i) Bestmann, H. J.; Moenius, T. Angew. Chem., Int. Ed. Engl. 1986, 25, 994. (j) Deardorft, D. R.; Shambayati, S.; Myles, D. C.; Heerding, D. J. Org. Chem. 1988, 53, 3614. (k) Hudlicky, T.; Luna, H. Barbieri, G.; Kwart, L. D. J. Am. Chem. Soc. 1988, 110, 4735.
29. For other methods of synthesis of 2,3-dihydroxy-4-cyclopentenones see: (d) Armstrong, A.; Hayter, B. R. Tetrahedron: Asymmetry 1997, 8, 1677. (e) Sundermann, B.; Scharf, H.-D. Tetrahedron: Asymmetry 1996, 7, 1995. (f) Johnson, C. R.; Esker, J. L.; Van Zandt, M. C. J. Org. Chem. 1994, 59, 5854. (g) Beer, D.; Meuwly, R.; Vasella, A. Helv. Chim. Acta 1982, 65, 2570. (h) Bélanger, P.; Prasit, P. Tetrahedron Lett. 1988, 29, 5521. (i) Bestmann, H. J.; Moenius, T. Angew. Chem., Int. Ed. Engl. 1986, 25, 994. (j) Deardorft, D. R.; Shambayati, S.; Myles, D. C.; Heerding, D. J. Org. Chem. 1988, 53, 3614. (k) Hudlicky, T.; Luna, H. Barbieri, G.; Kwart, L. D. J. Am. Chem. Soc. 1988, 110, 4735.
30. For other methods of synthesis of 2,3-dihydroxy-4-cyclopentenones see: (d) Armstrong, A.; Hayter, B. R. Tetrahedron: Asymmetry 1997, 8, 1677. (e) Sundermann, B.; Scharf, H.-D. Tetrahedron: Asymmetry 1996, 7, 1995. (f) Johnson, C. R.; Esker, J. L.; Van Zandt, M. C. J. Org. Chem. 1994, 59, 5854. (g) Beer, D.; Meuwly, R.; Vasella, A. Helv. Chim. Acta 1982, 65, 2570. (h) Bélanger, P.; Prasit, P. Tetrahedron Lett. 1988, 29, 5521. (i) Bestmann, H. J.; Moenius, T. Angew. Chem., Int. Ed. Engl. 1986, 25, 994. (j) Deardorft, D. R.; Shambayati, S.; Myles, D. C.; Heerding, D. J. Org. Chem. 1988, 53, 3614. (k) Hudlicky, T.; Luna, H. Barbieri, G.; Kwart, L. D. J. Am. Chem. Soc. 1988, 110, 4735.
31. For other methods of synthesis of 2,3-dihydroxy-4-cyclopentenones see: (d) Armstrong, A.; Hayter, B. R. Tetrahedron: Asymmetry 1997, 8, 1677. (e) Sundermann, B.; Scharf, H.-D. Tetrahedron: Asymmetry 1996, 7, 1995. (f) Johnson, C. R.; Esker, J. L.; Van Zandt, M. C. J. Org. Chem. 1994, 59, 5854. (g) Beer, D.; Meuwly, R.; Vasella, A. Helv. Chim. Acta 1982, 65, 2570. (h) Bélanger, P.; Prasit, P. Tetrahedron Lett. 1988, 29, 5521. (i) Bestmann, H. J.; Moenius, T. Angew. Chem., Int. Ed. Engl. 1986, 25, 994. (j) Deardorft, D. R.; Shambayati, S.; Myles, D. C.; Heerding, D. J. Org. Chem. 1988, 53, 3614. (k) Hudlicky, T.; Luna, H. Barbieri, G.; Kwart, L. D. J. Am. Chem. Soc. 1988, 110, 4735.
32. For other methods of synthesis of 2,3-dihydroxy-4-cyclopentenones see: (d) Armstrong, A.; Hayter, B. R. Tetrahedron: Asymmetry 1997, 8, 1677. (e) Sundermann, B.; Scharf, H.-D. Tetrahedron: Asymmetry 1996, 7, 1995. (f) Johnson, C. R.; Esker, J. L.; Van Zandt, M. C. J. Org. Chem. 1994, 59, 5854. (g) Beer, D.; Meuwly, R.; Vasella, A. Helv. Chim. Acta 1982, 65, 2570. (h) Bélanger, P.; Prasit, P. Tetrahedron Lett. 1988, 29, 5521. (i) Bestmann, H. J.; Moenius, T. Angew. Chem., Int. Ed. Engl. 1986, 25, 994. (j) Deardorft, D. R.; Shambayati, S.; Myles, D. C.; Heerding, D. J. Org. Chem. 1988, 53, 3614. (k) Hudlicky, T.; Luna, H. Barbieri, G.; Kwart, L. D. J. Am. Chem. Soc. 1988, 110, 4735.
33. For other methods of synthesis of 2,3-dihydroxy-4-cyclopentenones see: (d) Armstrong, A.; Hayter, B. R. Tetrahedron: Asymmetry 1997, 8, 1677. (e) Sundermann, B.; Scharf, H.-D. Tetrahedron: Asymmetry 1996, 7, 1995. (f) Johnson, C. R.; Esker, J. L.; Van Zandt, M. C. J. Org. Chem. 1994, 59, 5854. (g) Beer, D.; Meuwly, R.; Vasella, A. Helv. Chim. Acta 1982, 65, 2570. (h) Bélanger, P.; Prasit, P. Tetrahedron Lett. 1988, 29, 5521. (i) Bestmann, H. J.; Moenius, T. Angew. Chem., Int. Ed. Engl. 1986, 25, 994. (j) Deardorft, D. R.; Shambayati, S.; Myles, D. C.; Heerding, D. J. Org. Chem. 1988, 53, 3614. (k) Hudlicky, T.; Luna, H. Barbieri, G.; Kwart, L. D. J. Am. Chem. Soc. 1988, 110, 4735.
34. (a) Johnson, C.R. Pure Appl. Chem. 1987, 59, 969.
35. (b) Johnson, C. R.; Penning, T. D. J. Am. Chem. Soc. 1986, 108, 5655.
36. (c) Johnson, C. R.; Chen, Y.-F. J. Org. Chem. 1991, 56, 3344.
37. (d) Lim, M.-I.; Marquez, V. E. Tetrahedron Lett. 1983, 24, 5559.
38. (e) Medich, J. R.; Kunnen, K. B.; Johnson, C. R. Tetrahedron Lett. 1987, 28, 4131.
39. (f) Nokami, J.; Matsuura, H.; Takahashi, H.; Yamashita, M. Synlett 1994, 491.
40. (g) Hill, J. M.; Hutchinson, E. J.; Le Grand, D. M.; Roberts, S. M.; Thorpe, A. J.; Turner, N. J. J. Chem. Soc., Perkin Trans, 1 1994, 1483.
41. (h) Wolfe, M. S.; Anderson, B. L.; Borcherding, D. R.; Borchardt, R. T. J. Org. Chem. 1990, 55, 4712.
42. (i) Bestmann, H. J.; Roth, D. Synlett 1990, 751.
43. (j) Wang, P.; Agrofoglio, L. A.; Newton, M. G.; Chu, C. K. Tetrahedron Lett. 1997, 38, 4207.
44. (k) Roth, G. J.; Kirschbaum, S.; Bestmann, H. J. Synlett 1997, 618.
45. Aloui, M.; Lygo, B.; Trabsa, H. Synlett 1994, 115.
46. (b) Mirza, S.; Molleyres, L. P.; Vasella, A. Helv. Chim. Acta 1985, 68, 988.
47. (a) Ferrier, R. J. J. Chem. Soc., Perkin Trans, 1 1979, 1455.
48. For examples see: (b) Semeria, D.; Philippe, M.; Delaumeny, J. M.; Sepulchre, A. M.; Gero, S. D. Synthesis 1983, 710. (c) Bernet, B.; Vasella, A. Helv. Chim. Acta 1979, 64, 1990. (d) Jaramillo, C.; Chiara, J. L.; Martín-Lomas, M. J. Org. Chem. 1994, 59, 3135.
49. For examples see: (b) Semeria, D.; Philippe, M.; Delaumeny, J. M.; Sepulchre, A. M.; Gero, S. D. Synthesis 1983, 710. (c) Bernet, B.; Vasella, A. Helv. Chim. Acta 1979, 64, 1990. (d) Jaramillo, C.; Chiara, J. L.; Martín-Lomas, M. J. Org. Chem. 1994, 59, 3135.
50. For examples see: (b) Semeria, D.; Philippe, M.; Delaumeny, J. M.; Sepulchre, A. M.; Gero, S. D. Synthesis 1983, 710. (c) Bernet, B.; Vasella, A. Helv. Chim. Acta 1979, 64, 1990. (d) Jaramillo, C.; Chiara, J. L.; Martín-Lomas, M. J. Org. Chem. 1994, 59, 3135.
51. Timoshchuk, V. A. Russ. Chem. Rev. 1995, 64, 675.
52. (a) Dorta, R. L.; Francisco, C. G.; Freire, R.; Suárez, E. Tetrahedron Lett. 1988, 29, 5429.
53. (b) Dorta, R. L.; Francisco, C. G.; Suárez, E. Tetrahedron Lett. 1994, 35, 1083.
54. (c) Dorta, R. L.; Francisco, C. G.; Suárez, E. Tetrahedron Lett. 1994, 35, 2049.
55. Schmidt, R. R.; Hermetin, P. Chem. Ber. 1979, 112, 3616.
56. Neeman, M.; Johnson, W. S. Organic Syntheses; Wiley: New York, 1973; Coll. Vol. V, p 245.
57. Nakatani, K.; Arai, K.; Hirayama, N.; Matsuda, F.; Terashima, S. Tetrahedron 1992, 48, 633.
58. Kaskar, B.; Heise, G. L.; Michalak, R. S.; Vishnuvajjala, B. R. Synthesis 1990, 1031.
59. Corey, E. J.; Schmidt, G. Tetrahedron Lett. 1979, 5, 399.
60. Schmidt, R. R.; Jung, K.-H.; Hermetin, P. Chem. Ber. 1978, 3311.
61. Zhang, W.; Robins, M. J.; Tetrahedron Lett. 1992, 33, 1177.
62. Johansson, R.; Samuelsson, B. J. Chem. Soc., Perkin Trans, 1 1984, 2371.
63. Carbohydrates; Collins, P. M., Ed.; Chapman and Hall: London, 1987; p 301.