β-Fragmentation of primary alkoxyl radicals versus hydrogen abstraction: Synthesis of polyols and α,ω-differently substituted cyclic ethers from carbohydrates

Journal of Organic Chemistry

Volumn 68, Issue 13, 2003, Pages 5310-5319

  Boto, Alicia ^a   Hernández, Dácil ^a   Hernández, Rosendo ^a   Suárez, Ernesto ^a  

^a INSTITUTO DE PRODUCTOS NATURALES Y AGROBIOLOGÍA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

BIOLOGICAL ACTIVITIES;

CARBOHYDRATES; ETHERS; STEREOCHEMISTRY; SUBSTRATES;

AROMATIC COMPOUNDS;

CARBOHYDRATE; ETHER DERIVATIVE; HYDROGEN; NATURAL PRODUCT; POLYOL;

ARTICLE; FRAGMENTATION REACTION; MOLECULAR INTERACTION; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

ALCOHOLS; CARBOHYDRATES; COMBINATORIAL CHEMISTRY TECHNIQUES; ETHERS, CYCLIC; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; STEREOISOMERISM;

EID: 0038208388     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034442f     Document Type: Article

References (134)

1. (a) Zhdankin, V.; Stang, P. J. Chem. Rev. 2002, 102, 2523-2584.
2. (b) Hartung, J.; Gottwald, T.; Spehar, K. Synthesis 2002, 1469-1498.
3. (c) Togo, H.; Katohgi, M. Synlett 2001, 565-581.
4. (d) Suárez, E.; Rodríguez, M. S. In Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001; Vol. 2, pp 440-454.
5. (e) Zhang, W. In Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001; Vol. 2, pp 234-245.
6. (f) McCarroll, A. J.; Walton, J. C. Angew. Chem., Int. Ed. 2001, 40, 2224-2248.
7. (g) Wirth, T.; Hirt, U. H. Synthesis 1999, 1271-1287.
8. (h) Yet, L. Tetrahedron 1999, 55, 9349-9403.
9. (i) Varvoglis, A. Hypervalent Iodine in Organic Synthesis; Academic: New York, 1997.
10. (j) Brun, P.; Waegell, B. In Reactive Intermediates; Abramovitch, R. A., Ed.; Plenum Press: New York, 1983; Vol. 3, pp 367-426.
11. (k) Wilsey, S.; Dowd, P.; Houk, K. N. J. Org. Chem. 1999, 64, 8801-8811 and references therein.
12. For recent examples, see: (a) Deng, Y.; Snyder, J. K. J. Org. Chem. 2002, 67, 2864-2873.
13. (b) Barrero, A. F.; Oltra, J. E.; Alvarez, M.; Rosales, A. J. Org. Chem. 2002, 67, 5461-5469.
14. (c) Weavers, R. T. J. Org. Chem. 2001, 66, 6453-6461.
15. (d) Wang, X.; Porco, J. A., Jr. J. Org. Chem. 2001, 66, 8215-8221.
16. (e) Yoshimitsu, T.; Yanagisawa, S.; Nagaoka, H. Org. Lett. 2000, 2, 3751-3754.
17. (f) Boto, A.; Hernández, R.; Suárez, A. Tetrahedron Lett. 2000, 41, 2899-2902.
18. (g) Barrero, A. F.; Oltra, J. E.; Alvarez, M. Tetrahedron Lett. 2000, 41, 7639-7643.
19. (h) Wipf, P.; Li, W. J. Org. Chem. 1999, 64, 4576-4577.
20. (i) Mehta, G.; Mohal, N. Tetrahedron Lett. 1999, 40, 5791-5794.
21. (j) Rigby, J. H.; Meyer, J. H. Synlett 1999, 860-862.
22. (k) Wipf, P.; Li, W. J. Org. Chem. 1999, 64, 4576-4577.
23. (l) Armas, P.; García-Tellado, F.; Marrero-Tellado, J. J.; Robles, J. Tetrahedron Lett. 1998, 39, 131-134.
24. (m) Lautens, M.; Blackwell, J. Synthesis 1998, 537-546.
25. (n) Crimmins, M. T.; Wang, Z.; McKerlie, L. A. J. Am. Chem. Soc. 1998, 120, 1747-1756.
26. (o) Ziegler, F. E.; Wang, Y. J. Org. Chem. 1998, 63, 7920-7930.
27. (a) For other interesting examples, see: Boto, A.; Freire, R.; Hernández, R.; Suárez, E.; Rodríguez, M. S. J. Org. Chem. 1997, 62, 2975-2981.
28. (b) Oh, J. Tetrahedron Lett. 1997, 38, 3249-3250.
29. (c) Banwell, M. G.; Cameron, J. M. Tetrahedron Lett. 1996, 37, 525-526.
30. (d) Suginome, H.; Kondoh, T.; Gogonea, C.; Singh, V.; Goto, H.; Osawa, E. J. Chem. Soc., Perkin Trans. 1 1995, 69-81.
31. (e) Kim, H.; Ziani-Cherif, C.; Oh, J.; Cha, J. K. J. Org. Chem. 1995, 60, 729-793.
32. (f) Hernández, R.; Rodríguez, M. S.; Velázquez, S. M.; Suárez, E. J. Org. Chem. 1994, 59, 6395-6403.
33. (g) Suginome, H.; Nakayama, Y. Tetrahedron 1994, 50, 7771-7782.
34. (h) Lee, J.; Oh, J.; Jin, S.-j.; Choi, J.-R.; Atwood, J. L.; Cha, J. K. J. Org. Chem. 1994, 59, 6955-6964.
35. (i) Kobayashi, K.; Kanno, Y.; Seko, S.; Suginome, H. J. Chem. Soc., Perkin Trans. 1 1993, 825-829.
36. (j) Mowbray, C. E.; Pattenden, G. Tetrahedron Lett. 1993, 34, 127-130.
37. (k) Hayward, C. M.; Fisher, M. J.; Yohannes, D.; Danishefsky, S. J. Tetrahedron Lett. 1993, 34, 3989-3992.
38. (l) Chu-Moyer, M. Y.; Danishefsky, S. J. J. Am. Chem. Soc. 1992, 114, 8333-8334.
39. (m) Orito, K.; Yorita, K.; Suginome, H. Tetrahedron Lett. 1991, 32, 5999-6002.
40. (n) Mehta, G.; Krishnamurthy, N.; Karra, S. R. J. Am. Chem. Soc. 1991, 113, 5765-5775.
41. (o) Stork, G.; Mah, R. Tetrahedron Lett. 1989, 30, 3609-3612.
42. (p) Suginome, H.; Yamada, S. Chem. Lett. 1988, 245-248.
43. (q) Suginome, H.; Yamada, S. Tetrahedron Lett. 1987, 28, 3963-3966.
44. (r) Schreiber, S. L. J. Am. Chem. Soc. 1980,102, 6163-6165.
45. (s) Oh, J.; Lee, J.; Jin, S.-j.; Cha, J. K. Tetrahedron Lett. 1994, 35, 3449-3452.
46. (t) Snider, B. B.; Kwon, T. J. Org. Chem. 1992, 57, 2399-2410.
47. (a) Feray, L.; Kuznetsov, N.; Renaud, P. In Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001; Vol. 2, pp 246-278.
48. (b) Robertson, J.; Pillai, J.; Lush, R. K. Chem. Soc. Rev. 2001, 30, 94-103.
49. (c) Majetich, G.; Wheless, K. Tetrahedron 1995, 51, 7095-7129 and references therein.
50. (a) Aubele, D. L.; Floreancig, P. E. Org. Lett. 2002, 4, 3443-3446.
51. (b) Crich, D.; Huang, X.; Newcomb, M. J. Org. Chem. 2000, 65, 523-529.
52. (c) Chatgilialoglu, C.; Gimisis, T.; Spada, G. P. Chem.-Eur. J. 1999, 2866-2876.
53. (d) Allen, P. A.; Brimble, M. A.; Prabaharan, H. Synlett 1999, 295-298.
54. (e) Petrovic, G.; Saicic, R. N.; Cekovic, Z. Synlett 1999, 635-637.
55. (f) Frey, B.; Wells, A. P.; Rogers, D. H.; Mander, L. N. J. Am. Chem. Soc. 1998, 120, 1914-1915.
56. (g) Tsunoi, S.; Ryu, I.; Okuda, T.; Tanaka, M.; Komatsu, M.; Sonoda, N. J. Am. Chem. Soc. 1998, 120, 8692-8701.
57. (h) Dorta, R. L.; Martín, A.; Salazar, J. A.; Suárez, E.; Prangé, T. J. Org. Chem. 1998, 63, 2251-2261.
58. (i) Paquette, L. A.; Sun, L.-Q.; Friedrich, D.; Savage, P. B. J. Am. Chem. Soc. 1997, 119, 8438-8450.
59. (j) Burke, S. D.; Kort, M. E.; Strickland, S. M. S.; Organ, H. M.; Silks, L. A. Tetrahedron Lett. 1994, 35, 1503-1506.
60. (k) Danishefsky, S. J.; Armistead, D. M.; Wincott, F. E.; Selnick, H. G.; Hungate, R. J. Am. Chem. Soc. 1989, 111, 2967-2980.
61. (l) Titouani, S. L.; Lavergne, J.-P.; Viallefont, P.; Jacquier, R. Tetrahedron 1980, 36, 2961-2965.
62. (a) Hartung, J. Eur. J. Org. Chem. 2001, 619-632.
63. (b) Hartung, J. In Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001; Vol. 2, pp 427-439.
64. (c) For recent examples, see: Hartung, J.; Kneuer, R. Eur. J. Org. Chem. 2000, 1677-1683.
65. (d) Hartung, J.; Kneuer, R.; Spehar, K. Chem. Commun. 2001, 799-800.
66. (a) Buckmelter, A. J.; Rychnovsky, S. D. In Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001; Vol. 2, pp 334-349.
67. (b) Pearce, A. J.; Mallet, J.-M.; Sinay, P. In Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001; Vol. 2, pp 538-577.
68. (a) Boto, A.; Hernández, R.; Suárez, E. Tetrahedron Lett. 2001, 42, 9167-9170.
69. (b) Adinolfi, M.; Barone, G.; Iadonisi, A. Synlett 1999, 65-66.
70. (c) de Armas, P.; Francisco, C. G.; Suárez, E. Angew. Chem., Int. Ed. Engl. 1992, 31, 772-774.
71. (d) Inanaga, J.; Sigimoto, Y.; Yokoyama, Y.; Hanamoto, T. Tetrahedron Lett. 1992, 33, 8109-8112.
72. (a) Hartung, J.; Gottwald, T.; Kneuer, R. Synlett 2001, 749-752.
73. (b) Francisco, C. G.; León, E. I.; Martin, A.; Moreno, P.; Rodríguez, M. S.; Suárez, E. J. Org. Chem. 2001, 66, 6967-6976.
74. (a) Blunt, J. W.; Copp, B. R.; Munro, M. H. G.; Northcote, P. T.; Prinsep, M. R. Nat. Prod. Rep. 2003, 20, 1-48.
75. (b) Brenna, E.; Fuganti, C.; Serra, S. Tetrahedron: Asymmetry 2003, 14, 1-42.
76. (c) Hanson, J. R. Nat. Prod. Rep. 2003, 20, 70-78.
77. (d) Spivey, A. C.; Weston, M.; Woodhead, S. Chem. Soc. Rev. 2002, 31, 43-59.
78. (e) Fraga, B. M. Nat. Prod. Rep. 2002, 19, 650-672.
79. (f) Bruno, M.; Piozzi, F.; Rosselli, S. Nat. Prod. Rep. 2002, 19, 357-378.
80. (g) Hanson, J. R. Nat. Prod. Rep. 2002, 19, 125-132.
81. (h) Connolly, J. D.; Hill, R. A. Nat. Prod. Rep. 2002, 19, 494-513.
82. (i) Lewis, J. R. Nat. Prod. Rep. 2002, 19, 223-258.
83. (j) Jin, Z.; Li, Z.; Huang, R. Nat. Prod. Rep. 2002, 19, 454-476.
84. (k) Yeung, K. S.; Paterson, I. Angew. Chem., Int. Ed. 2002, 41, 4632-4653.
85. (l) Faulkner, D. J. Nat. Prod. Rep. 2002, 19, 1-48.
86. (m) Hale, K. J.; Hummersone, M. G.; Manaviazar, S.; Frigerio, M. Nat. Prod. Rep. 2002, 19, 413-453.
87. (n) Kalesse, M.; Christmann, M. Synthesis 2002, 981-1003.
88. (o) Paquette, L. A. ChemTracts 2002, 15, 345-366.
89. (p) Mann, J. Nat. Prod. Rep. 2001, 18, 417-430.
90. (q) Fernández, J. J.; Souto, M. L.; Norte, M. Nat. Prod. Rep. 2000, 17, 235-246.
91. (r) Murata, M.; Yasumoto, T. Nat. Prod. Rep. 2000, 17, 293-314.
92. (s) Brimble, M. A.; Nairn, M. R.; Prabaharan, H. Tetrahedron 2000, 56, 1937-1992.
93. (t) Vogel, P.; Cossy, J.; Plumet, J.; Arjona, O. Tetrahedron 1999, 55, 13521-13642.
94. (u) Figadère, B. Acc. Chem. Res. 1995, 28, 359-365.
95. (v) Dutton, C. J.; Banks, B. J.; Cooper, C. B. Nat. Prod. Rep. 1995, 165-181.
96. (x) Mori, K. Tetrahedron 1989, 45, 3233-3298.
97. (a) Barton, D. H. R.; Liu, W. Tetrahedron 1997, 53, 12067-12088.
98. (b) Aslani-Shotorbani, G.; Buchanan, J. G.; Edgar, A. R.; Shahidi, P. K. Carbohydr. Res. 1985, 136, 37-52.
99. Mariño-Albernas, J. R.; Verez-Bencomo, V.; Gonzalez, L.; Perez, C. S. Carbohydr. Res. 1987, 165, 197-206.
100. Duvold, T.; Francis, G. W.; Papaioannou, D. Tetrahedron Lett. 1995, 36, 3153-3156.
101. (a) Kaskar, B.; Heise, G. L.; Michalak, R. S.; Vishnuvajjala, B. R. Synthesis 1990, 1031-1032.
102. (b) Francisco, C. G.; González, C. C.; Suárez, E. J. Org. Chem. 1998, 63, 2099-2109.
103. Francisco, C. G.; Freire, R.; González, C. G.; León E. I.; Riesco-Fagundo, C.; Suárez, E. J. Org. Chem. 2001, 66, 1861-1866.
104. 3-H (δH 4.03).
105. The enantiomers of products 17 and 18 have been previously described: Collins, P. M.; Gupta, P.; Travis, A. S. J. Chem. Soc., Perkin Trans. 1 1980, 277-281.
106. de Armas, P.; Francisco, C. G.; Suárez, E. J. Am. Chem. Soc. 1993, 115, 8865-8866.
107. An example of the influence of the substituents on the relative rate of hydrogen abstraction versus β-fragmentation has been reported: Allen, P. R.; Brimble, M. A.; Farès, F. A. J. Chem. Soc., Perkin Trans. 1 1998, 2403-2411. (b) Francisco, C. G.; González, C.; Suárez, E. J. Org. Chem. 1998, 63, 8092-8093.
108. An example of the influence of the substituents on the relative rate of hydrogen abstraction versus β-fragmentation has been reported: Allen, P. R.; Brimble, M. A.; Farès, F. A. J. Chem. Soc., Perkin Trans. 1 1998, 2403-2411. (b) Francisco, C. G.; González, C.; Suárez, E. J. Org. Chem. 1998, 63, 8092-8093.
109. 4 was calculated to be -35°; the resulting J (about 5 Hz) would not match the experimental one.
110. Calculations using a MM2 force field model implanted in ChemBats3D ultra 6.0, CambridgeSoft.com.
111. 4-H.
112. 2-H have been isolated, since this abstraction was disfavored by steric and stereoelectronic factors. See also: (a) Francisco, C. G.; Herrera, A. J.; Suárez, E. J. Org. Chem. 2002, 67, 7439-7445. (b) Francisco, C. G.; Freire, R.; Herrera, A. J.; Pérez-Martín, I.; Suárez, E. Org. Lett. 2002, 4, 1959-1961. (c) Francisco, C. G.; Herrera, A. J.; Suárez, E. Tetrahedron Lett. 2000, 41, 7869-7873. (d) For studies on stereoelectronic effects in IHA reactions, see: Malatesta, V.; Ingold, K. U. J. Am. Chem. Soc. 1981, 103, 609-614. (e) Beckwith, A. L. J.; Easton, C. J. J. Am. Chem. Soc. 1981, 103, 615-619.
113. 2-H have been isolated, since this abstraction was disfavored by steric and stereoelectronic factors. See also: (a) Francisco, C. G.; Herrera, A. J.; Suárez, E. J. Org. Chem. 2002, 67, 7439-7445. (b) Francisco, C. G.; Freire, R.; Herrera, A. J.; Pérez-Martín, I.; Suárez, E. Org. Lett. 2002, 4, 1959-1961. (c) Francisco, C. G.; Herrera, A. J.; Suárez, E. Tetrahedron Lett. 2000, 41, 7869-7873. (d) For studies on stereoelectronic effects in IHA reactions, see: Malatesta, V.; Ingold, K. U. J. Am. Chem. Soc. 1981, 103, 609-614. (e) Beckwith, A. L. J.; Easton, C. J. J. Am. Chem. Soc. 1981, 103, 615-619.
114. 2-H have been isolated, since this abstraction was disfavored by steric and stereoelectronic factors. See also: (a) Francisco, C. G.; Herrera, A. J.; Suárez, E. J. Org. Chem. 2002, 67, 7439-7445. (b) Francisco, C. G.; Freire, R.; Herrera, A. J.; Pérez-Martín, I.; Suárez, E. Org. Lett. 2002, 4, 1959-1961. (c) Francisco, C. G.; Herrera, A. J.; Suárez, E. Tetrahedron Lett. 2000, 41, 7869-7873. (d) For studies on stereoelectronic effects in IHA reactions, see: Malatesta, V.; Ingold, K. U. J. Am. Chem. Soc. 1981, 103, 609-614. (e) Beckwith, A. L. J.; Easton, C. J. J. Am. Chem. Soc. 1981, 103, 615-619.
115. 2-H have been isolated, since this abstraction was disfavored by steric and stereoelectronic factors. See also: (a) Francisco, C. G.; Herrera, A. J.; Suárez, E. J. Org. Chem. 2002, 67, 7439-7445. (b) Francisco, C. G.; Freire, R.; Herrera, A. J.; Pérez-Martín, I.; Suárez, E. Org. Lett. 2002, 4, 1959-1961. (c) Francisco, C. G.; Herrera, A. J.; Suárez, E. Tetrahedron Lett. 2000, 41, 7869-7873. (d) For studies on stereoelectronic effects in IHA reactions, see: Malatesta, V.; Ingold, K. U. J. Am. Chem. Soc. 1981, 103, 609-614. (e) Beckwith, A. L. J.; Easton, C. J. J. Am. Chem. Soc. 1981, 103, 615-619.
116. 2-H have been isolated, since this abstraction was disfavored by steric and stereoelectronic factors. See also: (a) Francisco, C. G.; Herrera, A. J.; Suárez, E. J. Org. Chem. 2002, 67, 7439-7445. (b) Francisco, C. G.; Freire, R.; Herrera, A. J.; Pérez-Martín, I.; Suárez, E. Org. Lett. 2002, 4, 1959-1961. (c) Francisco, C. G.; Herrera, A. J.; Suárez, E. Tetrahedron Lett. 2000, 41, 7869-7873. (d) For studies on stereoelectronic effects in IHA reactions, see: Malatesta, V.; Ingold, K. U. J. Am. Chem. Soc. 1981, 103, 609-614. (e) Beckwith, A. L. J.; Easton, C. J. J. Am. Chem. Soc. 1981, 103, 615-619.
117. (a) For a preliminary communication of this work, see: Boto, A.; Hernández, R.; Suárez, E. Tetrahedron Lett. 2002, 43, 1821-1824.
118. (b) For a related work from our group where acyloxyaldoses were formed from uronic acids, see: Francisco, C. G.; González, C. C.; Suárez, E. Tetrahedron Lett. 1997, 38, 4141-4144.
119. (a) Bishop, R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 6, pp 261-300.
120. (b) Kita, Y.; Shibata, N.; Kawano, N.; Yoshida, N.; Matsumoto, K.; Takebe, Y. J. Chem. Soc., Perkin Trans. 1 1996, 2321-2329.
121. Csuk, R.; Kühn, M.; Schöhl, D. Tetrahedron 1997, 53, 1311-1322.
122. (a) Krause, N.; Hoffmann-Röder, A.; Canisius, J. Synthesis 2002, 1759-1774.
123. (b) Nicolaou, K. C.; Mitchell, H. J. Angew. Chem., Int. Ed. 2001, 40, 1576-1624.
124. (c) Lee, E. In Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001; Vol. 2, pp 303-333.
125. (d) Brimble, M. A.; Farès, F. A. Tetrahedron 1999, 55, 7661-7706.
126. (e) Hoberg, J. O. Tetrahedron 1998, 54, 12631-12670.
127. (f) Hoppe, R.; Scharf, H. D. Synthesis 1995, 1447-1464.
128. (g) Harmange, J. C.; Figadère, B. Tetrahedron: Asymmetry 1993, 4, 1711-1754.
129. Keck, G. E.; Yates, J. B. J. Am. Chem. Soc. 1982, 104, 5831-5833.
130. (a) For a review, see: Schmidt, R. R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 6, pp 33-64.
131. (b) For a recent work, see: Pilli, R. A.; Riatto, V. B. Tetrahedron: Asymmetry 2000, 11, 3675-3686 and references therein.
132. (a) Giese, B.; Linker, T. Synthesis 1992, 46-48.
133. (b) Ferrier, R. J.; Tyler, P. C. J. Chem. Soc., Perkin Trans. 1 1980, 2767-2773.
134. Perrin, D. D.; Armarego, W. L. F. Purification of Laboratory Chemicals, 3rd ed.; Pergamon Press: New York, 1988.