Diastereoselective synthesis of all eight L-hexoses from L-ascorbic acid

Journal of Organic Chemistry

Volumn 71, Issue 2, 2006, Pages 693-703

  Ermolenko, Ludmila ^a   Sasaki, N André ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATES; HYDROXYLATION; OLEFINS; RATE CONSTANTS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

ASCORBIC ACID; DIASTEREOMERS; DIOL FORMATION; WITTIG OLEFINATION REACTIONS;

CARBOXYLIC ACIDS;

2 HYDROXYACID; ASCORBIC ACID; GLYCOL; HEXOSE;

ARTICLE; CHEMICAL REACTION KINETICS; CHIRALITY; DIASTEREOISOMER; DIHYDROXYLATION; HORNER REACTION; LIGAND BINDING; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

ASCORBIC ACID; HEXOSES; INDICATORS AND REAGENTS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; STEREOISOMERISM;

EID: 30744454015     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0521192     Document Type: Article

References (66)

1. Stack, R. J. FEMS Microbiol. Lett. 1987, 48, 83-87.
2. Dondoni, A.; Marra, A.; Massi, A. J. Org. Chem. 1997, 62, 6261-6267.
3. van Boeckel, C. A. A.; Beetz, T.; Vos, A. J. M.; de Jong, A. J. M.; van Aelst, S. F.; van den Bosch, R. H.; Mertens, J. M. R.; van der Vlugt, F. A. J. Carbohydr. Chem. 1985, 4, 293-321.
4. Prabhu, A.; Venot, A.; Boons, G.-J. Org. Lett. 2003, 26, 4975-4978.
5. Lee, J.-C.; Chang, S.-W.; Liao, C.-C.; Chi, F.-C.; Chen, C.-S.; Wen, Y.-S.; Wang, C.-C.; Kulkarni, S. S.; Puranik, R.; Liu, Y.-H.; Hung, S.-C. Chem. Eur. J. 2004, 10, 399-415.
6. Kovensky, J.; Duchaussoy, P.; Bono, F.; Salmivirta, M.; Sizun, P.; Herbert, J.-M.; Petitou, M.; Sinay, P. Biorg. Med. Chem. 1999, 7, 1567-1580.
7. Kubelka, W. Phytochemistry 1974, 13, 1805-1808.
8. Guttiérrez, M.; Capson, T.; Guzmán, H. M.; Quiñoá, E.; Riguera, R. Tetrahedron Lett. 2004, 45, 7833-7836.
9. (a) Shallenberger, R. S.; Acree, T. E.; Lee, C. Y. Nature 1961, 221, 555-556.
10. (b) Levin, G. V. U.S. Patent 4262032. 1981.
11. Tarka Jr., S. M.; Shively, C. A.; Apgar, J. L.; Koch, K. L. U.S. Patent 5219573, 1989.
12. Levin, G. V.; Zehner. L. R. U.S. Patent 5166193, 1992.
13. (a) Humoller, F. L.; Frush, H. L.; Isbell, H. S.; Sowden, J. C.; Whistler, R. L.; BeMiller, J. N.; Shafizaden, F. In Methods in Carbohydrate Chemistry, Academic Press: New York, 1962: Vol. 1, pp 105-145.
14. (b) Evans, M. E.; Parrish, F. W.; Blanc-Muesser, M.; DeFaye, J.; Horton, D.; Tsai, J.-H. In Methods in Carbohydrate Chemistry; Academic Press: New York, 1980; Vol. VIII, pp 173-185.
15. (c) Hudlicky, T.; Enlwistle, D. A.; Pitzer, K. K.; Thorpe, A. J. Chem. Rev. 1996, 96, 1195-1220 and references therein.
16. (d) Hung, S.-C.; Wang, C.-C.; Chang, S.-W.; Chen, C.-S. Tetrahedron Lett. 2001, 42, 1321-1324.
17. (e) Hung, S.-C.; Wang, C.-C.; Thopate, S. R. Tetrahedron Lett. 2000, 41, 3119-3122.
18. (f) Harris, J. M.; Keränen, M. D.; Nguyen, H.; Yong, V. G.; O'Doherty, G. A. Carbohydr. Res. 2000, 328, 17-36.
19. (g) Adinolfi, M.; Barone, G.; De Lorenzo, F.; Iadonisi, A. Synlett 1999, 3, 336-338.
20. (h) Hajkó, J.; Lipták, A.; Pozsgay, V. Carbohydr. Res. 1999, 321, 116-120.
21. (i) Tletze, L. F.; Montenbruck, A.; Schneider, C. Synlett 1994, 509-510.
22. (j) Bazin, H. G.; Wolff, M. W.; Linhardt, R. J. J. Org. Chem, 1999, 64, 144-152.
23. (k) Harris, J. M.; Keränen, M. D.; O'Doherty, G. A. J. Org. Chem, 1999, 64, 2982-2983.
24. Takahashi, H.; Hitomi, Y.; Iwai, Y.; Ikegami, S. J. Am. Chem. Soc. 2000, 122, 2995-2998.
25. Northrup, A. B.; MacMillan, D. W. C. Science 2004, 1752-1755.
26. (n) Ahmed, Md. M.; Berry, B. P.; Hunter, T. J.; Tomcik, D. J.; O'Doherty, G. A. Org. Lett. 2005, 7, 745-748.
27. Ko, S. Y.; Lee, A. W. M.; Masamune, S.; Reed, L. A., III; Sharpless, K. B.; Walker, F. J. Tetrahedron 1990, 46, 245-264.
28. (a) Takeuchi, M.; Teniguchi, T.; Ogasawara, K. Synthesis 1999, 2, 341-354.
29. (b) Takeuchi, M.; Taniguchi, T.; Ogasawara, K. Chirality 2000, 338-341.
30. Ermolenko, L.; Sasaki, N. A.; Potier P. Helv. Chim. Acta 2003, 86, 3578-3582.
31. Abushanab, E.; Vemishetti, P.; Leiby, R. W.; Singh, H. K.; Mikkilineni, A. B.; Wu, D. C.-J.; Saibaba, R.; Panzica, R. P. J. Org. Chem. 1988, 53, 2598-2602.
32. Saïah, M.; Bessodes, M.; Antonakis, K. Tetrahedron Lett. 1992, 33, 4317-4320.
33. Nakajima, N.; Horita, K.; Abe, R.; Yonemitsu, O. Tetrahedron Lett. 1988, 29, 4139-4142.
34. Bouzide, A.; Sauvé, G. Tetrahedron Lett. 1997, 38, 5945-5948.
35. André, C.; Bolte J.; Demuynek C. Tetrahedron: Asymmetry 1998, 9, 1359-1367.
36. Soai, K.; Ookawa, A. J. Org. Chem. 1986, 51, 4000-4005.
37. (a) Mulzer, J.; Kappert, M. Angew. Chem., Int. Ed. Engl. 1983, 22, 63-64.
38. (b) Mulzer, J.; Kappert, M. Angew. Chem. Suppl. 1982, 22, 23-33.
39. (c) Hu, T.-S.; Yu, Q.; Wu, Y.-L.; Wu, Y. J. Org. Chem. 2001, 66, 853-861.
40. (a) Sánchez-Sancho, P.; Valverde, S.; Herradón, B. Tetrahedron: Asymmetry 1996, 7, 3209-3246.
41. (b) Valverde, S.; Martin-Lomas, M.; Herradón, B.; Garcia-Ochoa, S. Tetrahedron 1987, 43, 1895-1901.
42. (a) Katsuki, T.; Lee, A. W. M.; Ma, P.; Martin, V., S.; Masamune, S.; Sharpless, K. B.; Tuddenham, D.; Walker, F. J. J. Org. Chem. 1982, 47, 1373-1378.
43. (b) Minami, N.; Ko, S. S.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 1109-1111.
44. (c) Trost, B. M.; Lynch, J.; Renaut, P.; Steinman, D. H. J. Am. Chem. Soc. 1986, 108, 284-291.
45. Larsen, R. O.; Aksnes, G. Phosphorus Sulfur 1983, 16, 339-344.
46. Still, W. C.; Gennari, C. Tetrahedron Lett. 1983, 24, 4405-4408.
47. (a) Christ, W. C.; Cha, J. K.; Kishi, Y. Tetrahedron Lett. 1983, 24, 3947-3950.
48. (b) Stork, G.; Kahn, M. Tetrahedron Lett. 1983, 24, 3951-3954.
49. Cha, J. K.; Christ, W. C.; Kishi, Y. Tetrahedron 1984, 40, 2247-2255.
50. (a) Saito, S.; Morikawa, Y.; Moriwake, T. J. Org. Chem. 1990, 55, 5424-5426.
51. (b) Brimacombe, J. S.; Hanna, R.; Kabir, A. K. M. S.; Bennet, F.; Taylor, I. D. J. Chem. Soc., Perkin Trans, 1 1986, 815-821.
52. (c) Izquierdo, I.; Plaza, M. T.; Robles, R.; Rodriguez, C. Tetrahedron: Asymmetry 1996, 7, 3593-3604.
53. (d) DeNinno, M. P.; Donishefsky, S. J.; Schulte, G. J. Am. Chem. Soc. 1988, 110, 3925-3929.
54. (e) Evans, D. A.; Kaldor, S. W. J. Org. Chem. 1990, 55, 1698-1670.
55. (f) Annunziata, R.; Cinquini, M.; Cozzi, F.; Raimondi, L. Tetrahedron 1988, 44, 6897-6902.
56. (e) Jorgensen, M.; Iversen, E. H.; Madsen, R. J. Org. Chem. 2001, 68, 4625-4629.
57. 4/NMO dihydroxylation of TBDPS-protected analogues of 9, 10, 11, and 12, the diols were produced in ratios 90:10, 85:15, 30:70, and 40:60, respectively.
58. Brimacombe, J. S.; McDonald, G.; Abdur Rahman, M. Carbohydr. Res. 1990, 205, 422-427.
59. (a) Wang, L.; Sharpless, K. B. J. Am. Chem. Soc. 1992, 114, 7568-7570.
60. (b) Xu, D.; Crispino, G. A.; Sharpless, K. B. J. Am. Chem. Soc. 1992, 114, 7570-7571.
61. (c) Morikawa, K.; Sharpless K., B. Tetrahedron Lett. 1993, 34, 5575-5578.
62. (d) Ziegler, F. E.; Wang, Y. J. Org. Chem. 1998, 63, 7920-7930.
63. (e) Kim, N.-S.; Choi, J.-R.; Cha, J. K. J. Org. Chem. 1993, 58, 7096-7099.
64. (f) Abdur Rahman, M.; Adams, J. P.; Boyes, A. L.; Kelly M. J.; Mansfield, D. J.; Procopiou, P. A.; Roberts, S. M.; Slee, D. H.; Sidebottom, P. J.; Sik, V.; Watson, N. S. J. Chem. Soc., Chem. Commun. 1993, 1841-1843.
65. Bock, K.; Thogersen, H. Annu. Rep. NMR Spectrosc. 1982, 13, 1-57.
66. Ermolenko, L.; Sasaki, N. A.; Potier, P. J. Chem. Soc., Perkin Trans. 1 2000, 2465-2473.