Synthetic strategies directed towards 5a-carbahexopyranoses and derivatives based on 6-endo-trig radical cyclizations

European Journal of Organic Chemistry

Volumn , Issue 35, 2011, Pages 7116-7132

  Gómez, Ana M ^a   Uriel, Clara ^a   Company, Maria D ^a   López, J Cristóbal ^a  

^a INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

Author keywords

Carbasugars; Carbohydrates; Cyclization; Ozonation; Radicals; Regioselectivity

Indexed keywords

EID: 82455205772     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201100956     Document Type: Article

References (127)

1. G. E. McCasland, S. Furuta, L. J. Durham, J. Org. Chem. 1966, 31, 1516-1518.
2. Carbohydrate Mimics. Concepts and Methods (Ed.:, Y. Chapleur), Wiley-VCH, Weinheim, Germany, 1998.
3. P. Sears, C.-H. Wong, Angew. Chem. 1999, 111, 2446
4. Angew. Chem. Int. Ed. 1999, 38, 2300-2324.
5. G. E. McCasland, S. Furuta, L. J. Durham, J. Org. Chem. 1968, 33, 2841-2844.
6. G. E. McCasland, S. Furuta, L. J. Durham, J. Org. Chem. 1968, 33, 2835-2840.
7. T. W. Miller, B. H. Arison, G. Albers-Schonberg, Biotechnol. Bioeng. 1973, 15, 1075-1080.
8. P. M. Rudd, T. Elliott, P. Cresswell, I. A. Wilson, R. A. Dwek, Science 2001, 291, 2370-2376.
9. A. Helenius, M. Aebi, Science 2001, 291, 2364-2369.
10. M. Hricovini, Curr. Med. Chem. 2004, 11, 2565-2583.
11. C. R. Bertozzi, L. L. Kiessling, Science 2001, 291, 2357-2364.
12. P. Sears, C.-H. Wong, Cell Mol. Life Sci. 1998, 54, 223-252.
13. H. Lis, N. Sharon, Eur. J. Biochem. 1993, 218, 1-27.
14. A. Varki, Glycobiology 1993, 3, 97-130.
15. B. Ernst, Chimia 1999, 53, 193-194.
16. J. Plumet, A. M. Gómez, J. C. López, Mini-Rev. Org. Chem. 2007, 4, 201-216.
17. S. Ogawa, Trends Glycosci. Glycotechnol. 2004, 16, 33-53.
18. T. Suami, Top. Curr. Chem. 1990, 154, 257-283.
19. T. Suami, S. Ogawa, Adv. Carbohydr. Chem. Biochem. 1990, 48, 21-90.
20. T. Suami, Pure Appl. Chem. 1987, 59, 1509-1520.
21. S. Ogawa, in: Studies in Natural Product Chemistry (Ed.: Atta-ur-Rahman); Elsevier, New York, 1993, p. 187.
22. S. Ogawa, in: Carbohydrate and Drug Design (Eds.:, Z. J. Witczak, K. A. Nieforth), Marcel Dekker, New York, 1997, p. 433.
23. Y. Kobayashi, in: Glycoscience (Eds.:, B. Fraser-Reid, K. Tatsuta, J. Thiem), Springer, Heidelberg, Germany, 2001, p. 2595.
24. O. Arjona, A. M. Gómez, J. Plumet, J. C. López, Chem. Rev. 2007, 107, 1919-2036.
25. J. C. López, B. Fraser-Reid, Chem. Commun. 1997, 2251-2257.
26. A. M. Gómez, S. Mantecón, S. Valverde, J. C. López, J. Org. Chem. 1997, 62, 6612-6614.
27. A. M. Gómez, J. C. López, B. Fraser-Reid, J. Org. Chem. 1994, 59, 4048-4050.
28. J. C. López, A. M. Gómez, B. Fraser-Reid, J. Chem. Soc., Chem. Commun. 1994, 1533-1534.
29. J. C. López, A. M. Gómez, S. Valverde, J. Chem. Soc., Chem. Commun. 1992, 613-615.
30. Joint Commission on Biochemical Nomenclature (A. D. McNaught, Pure Appl. Chem. 1996, 68, 1919-2008).
31. L. Andersson, B. Classon, B. Samuelsson, J. Org. Chem. 1990, 55, 4699-4704.
32. W. Schmid, G. M. Whitesides, J. Am. Chem. Soc. 1990, 112, 9670-9671.
33. H. Redlich, W. Sudau, A. K. Szardenings, R. Vollerthun, Carbohydr. Res. 1992, 226, 57-78.
34. J. Marco-Contelles, C. Pozuelo, M. L. Jimeno, L. Martínez, A. Martínez-Grau, J. Org. Chem. 1992, 57, 2625-2631.
35. E. Maudru, G. Singh, R. H. Wightman, Chem. Commun. 1998, 1505-1506.
36. A. K. Szardenings, R. Vollerthun, P. Kipke, H. Redlich, Eurocarb9, July, 1997, Abstract A184, abstract book, p. 264.
37. A. M. Gómez, G. O. Danelón, E. Moreno, S. Valverde, J. C. López, Chem. Commun. 1999, 175-176.
38. A. M. Gómez, E. Moreno, S. Valverde, J. C. López, Synlett 2002, 891-894.
39. A. M. Gómez, E. Moreno, S. Valverde, J. C. López, Tetrahedron Lett. 2002, 43, 5559-5562.
40. A. M. Gómez, G. O. Danelón, E. Moreno, S. Valverde, J. C. López, Tetrahedron: Asymmetry 2003, 14, 2961-2974.
41. A. M. Gómez, E. Moreno, S. Valverde, J. C. López, Eur. J. Org. Chem. 2004, 1830-1840.
42. R. K. Shrivastava, E. Maudru, G. Singh, R. H. Wightman, K. M. Morgan, Beilstein, J. Org. Chem. 2008, 4, No. 43.
43. A. L. J. Beckwith, Tetrahedron 1981, 37, 3073-3100, and references therein.
44. D. P. Curran, N. A. Porter, B. Giese, Stereochemistry of Radical Reactions-Concepts. Guidelines and Synthetic Applications, Weinheim, Germany, 1996.
45. J. Fossey, D. Lefort, J. Sorba, Free Radicals in Organic Chemistry, John Wiley & Sons, Chichester, England, 1995.
46. A. L. J. Beckwith, Chem. Soc. Rev. 1993, 22, 143-151.
47. T. V. RajanBabu, Acc. Chem. Res. 1991, 24, 139-145.
48. B. Giese, Angew. Chem. 1983, 95, 771
49. Angew. Chem. Int. Ed. Engl. 1983, 22, 753-764.
50. M. Julia, Acc. Chem. Res. 1971, 4, 386-392.
51. B. Giese, in: Radicals in Organic Synthesis: Formation of Carbon Carbon Bonds (Ed.:, J. E. Baldwin), Pergamon, New York, 1986.
52. F. Portela-Cubillo, R. Alonso-Ruiz, D. Sampedro, J. C. Walton, J. Phys. Chem. A 2009, 113, 10005-10012.
53. C. Zhou, O. Plashkevych, J. Chattopadhyaya, Org. Biomol. Chem. 2008, 6, 4627-4633.
54. T. Taniguchi, D. Yonei, M. Sasaki, O. Tamura, H. Ishibashi, Tetrahedron 2008, 64, 2634-2641.
55. F. Liu, K. Liu, X. Yuan, C. Li, J. Org. Chem. 2007, 72, 10231-10234.
56. H. Ishibashi, Chem. Rec. 2006, 6, 23-31.
57. E. W. Della, S. D. J. Graney, J. Org. Chem. 2004, 69, 3824-3835.
58. J. Cassayre, F. Gagosz, S. Z. Zard, Angew. Chem. 2002, 114, 1861
59. Angew. Chem. Int. Ed. 2002, 41, 1783-1785.
60. E. W. Della, C. Kostakis, P. A. Smith, Org. Lett. 1999, 1, 363-365.
61. D. E. Ward, Y. Gai, B. F. Kaller, J. Org. Chem. 1995, 60, 7830-7836.
62. P. F. Keusenkothen, M. B. Smith, Tetrahedron 1992, 48, 2977-2992.
63. J. Marco-Contelles, M. Bernabe, D. Ayala, B. Sanchez, J. Org. Chem. 1994, 59, 1234-1235.
64. D. E. Ward, B. F. Kaller, Tetrahedron Lett. 1991, 32, 843-846.
65. S. Knapp, F. S. Gibson, Y. H. Choe, Tetrahedron Lett. 1990, 31, 5397-5400.
66. A. Padwa, H. Nimmesgern, G. S. K. Wong, J. Org. Chem. 1985, 50, 5620-5627.
67. A. L. J. Beckwith, I. A. Blair, G. Philipou, Tetrahedron Lett. 1974, 15, 2251-2254.
68. A. L. J. Beckwith, T. Lawrence, J. Chem. Soc. Perkin Trans. 2 1979, 1535-1539.
69. A. L. J. Beckwith, D. M. O'Shea, Tetrahedron Lett. 1986, 27, 4525-4528.
70. G. Stork, R. Mook Jr., Tetrahedron Lett. 1986, 27, 4529-4532.
71. A. M. Gómez, M. D. Company, C. Uriel, S. Valverde, J. C. López, Tetrahedron Lett. 2002, 43, 4997-5000.
72. U. Albrecht, R. Wartchow, H. M. R. Hoffmann, Angew. Chem. 1992, 104, 903
73. Angew. Chem. Int. Ed. Engl. 1992, 31, 910-913.
74. H. M. R. Hoffmann, U. Herden, M. Breithor, O. Rhode, Tetrahedron 1997, 53, 8383-8400.
75. M. Breithor, U. Herden, H. M. R. Hoffmann, Tetrahedron 1997, 53, 8401-8420.
76. A. M. Gómez, G. O. Danelón, S. Valverde, J. C. López, J. Org. Chem. 1998, 63, 9626-9627.
77. A. M. Gómez, M. D. Company, C. Uriel, S. Valverde, J. C. López, Tetrahedron Lett. 2007, 48, 1645-1649.
78. G. Stork, N. H. Baine, J. Am. Chem. Soc. 1982, 104, 2321-2323.
79. G. Stork, R. Mook Jr., J. Am. Chem. Soc. 1983, 105, 3720-3722.
80. G. Stork, N. H. Baine, Tetrahedron Lett. 1985, 26, 5927-5930.
81. G. Stork, R. Mook Jr., J. Am. Chem. Soc. 1987, 109, 2829-2831.
82. M. Mella, L. Panza, F. Ronchetti, L. Toma, Tetrahedron 1988, 44, 1673-1678.
83. A. M. Gómez, G. O. Danelón, S. Valverde, J. C. López, Carbohydr. Res. 1999, 320, 138-142.
84. A. J. Mancuso, D. Swern, Synthesis 1981, 165-185.
85. D. B. Dess, J. C. Martin, J. Org. Chem. 1983, 48, 4155-4156.
86. F. Andersson, B. Samuelsson, Carbohydr. Res. 1984, 129, C1-C3.
87. F. N. Tebbe, G. W. Parshall, G. S. Reddy, J. Am. Chem. Soc. 1978, 100, 3611-3613.
88. L. Lombardo, Tetrahedron Lett. 1982, 23, 4293-4296.
89. D. J. Peterson, J. Org. Chem. 1968, 33, 780-784.
90. For an authoritative review on the synthetic potential of carbohydrate-derived stannanes, see:, S. Jarosz, A. Gawel, Eur. J. Org. Chem. 2005, 3415-3432.
91. C. Taillefumier, Y. Chapleur, Chem. Rev. 2004, 104, 263-292.
92. R. J. K. Taylor, Chem. Commun. 1999, 217-227.
93. T. Suami, S. Ogawa, K. Nakamoto, I. Kasahara, Carbohydr. Res. 1977, 58, 240-244.
94. S. Ogawa, M. Ara, T. Kondoh, M. Saitoh, R. Masuda, T. Toyokuni, T. Suami, Bull. Chem. Soc. Jpn. 1980, 53, 1121-1126.
95. S. Ogawa, Y. Iwasawa, T. Suami, Chem. Lett. 1984, 355-356.
96. S. Ogawa, Y. Iwasawa, T. Nose, T. Suami, S. Ohba, M. Ito, Y. Saito, J. Chem. Soc. Perkin Trans. 1 1985, 903-906.
97. H. Paulsen, W. von Deyn, Liebigs Ann. Chem. 1987, 125-131.
98. S. Ogawa, H. Aoyama, T. Sato, Carbohydr. Res. 2002, 337, 1979-1992.
99. dl -mixture:, T. Suami, S. Ogawa, T. Ishibashi, I. Kasahara, Bull. Chem. Soc. Jpn. 1976, 49, 1388-1390.
100. J. Gelas, D. Horton, Carbohydr. Res. 1978, 67, 371-387.
101. P. Ermert, A. Vasellla, M. Weber, K. Rupitz, S. G. Withers, Carbohydr. Res. 1993, 250, 113-128.
102. S. Koto, N. Morishima, Y. Miyata, S. Zen, Bull. Chem. Soc. Jpn. 1976, 49, 2639-2640.
103. P. Girard, J. L. Namy, H. B. Kagan, J. Am. Chem. Soc. 1980, 102, 2693-2698.
104. G. A. Molander, C. R. Harris, Chem. Rev. 1996, 96, 307-338.
105. D. J. Edmonds, D. Johnston, D. J. Procter, Chem. Rev. 2004, 104, 3371-3403.
106. K. C. Nicolaou, S. P. Ellery, J. S. Chen, Angew. Chem. 2009, 121, 7276
107. Angew. Chem. Int. Ed. 2009, 48, 7140-7165.
108. S. Ogawa, Y. Iwasawa, T. Nose, T. Suami, S. Ohba, M. Ito, Y. Saito, J. Chem. Soc. Perkin Trans. 1 1985, 903-906.
109. H. Staudinger, E. Hauser, Helv. Chim. Acta 1921, 4, 861-886.
110. E. F. V. Scriven, K. Turnbull, Chem. Rev. 1988, 88, 297-368.
111. Y. G. Gololobov, L. F. Kasukhin, Tetrahedron 1992, 48, 1353-1406.
112. I. Bosch, F. Urpi, J. Vilarrasa, J. Chem. Soc., Chem. Commun. 1995, 91-92.
113. I. Bosch, A. González, F. Urpí, J. Vilarrasa, J. Org. Chem. 1996, 61, 5638-5643.
114. J. J. Garcia-Lopez, F. Santoyo-Gonzalez, A. Vargas-Berenguel, Synlett 1997, 265-266.
115. A similar transformation has been reported:, G. Campiani, L. Q. Sun, A. P. Kozikowski, P. Aagaard, M. McKinney, J. Org. Chem. 1993, 58, 7660-7669.
116. J. L. Aceña, E. Alba, O. Arjona, J. Plumet, Tetrahedron Lett. 1996, 37, 3043-3044.
117. J. L. Aceña, O. Arjona, J. Plumet, J. Org. Chem. 1997, 62, 3360-3364.
118. A. M. Gómez, M. D. Company, S. Valverde, J. C. López, Org. Lett. 2002, 4, 383-386.
119. R. Criegee, Angew. Chem. 1975, 87, 765
120. Angew. Chem. Int. Ed. Engl. 1975, 14, 745-752.
121. R. L. Kuczkowski, Acc. Chem. Res. 1983, 16, 42-47.
122. R. L. Kuczkowski, Chem. Soc. Rev. 1992, 21, 79-83.
123. G. Büchi, H. Wüest, J. Am. Chem. Soc. 1978, 100, 294-295.
124. M. A. Avery, C. Jennings-White, W. K. M. Chong, Tetrahedron Lett. 1987, 28, 4629-4632.
125. M. A. Avery, W. K. M. Chong, C. Jennings-White, J. Am. Chem. Soc. 1992, 114, 974-979.
126. K. Nozaki, K. Oshima, K. Utimoto, J. Am. Chem. Soc. 1987, 109, 2547-2549.
127. K. Nozaki, K. Oshima, K. Utimoto, Tetrahedron 1989, 45, 923-933.