Synthesis of furanosyl C-1 glycals through palladium-catalyzed reactions of a furanosyl 2,3-anhydro-exe-glycal

European Journal of Organic Chemistry

Volumn , Issue 27, 2009, Pages 4627-4636

  Gómez, Ana M ^a   Pedregosa, Ana ^a   Barrio, Aitor ^a   Valverde, Serafín ^a   Cristobal Lopez J ^a  

^a INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

Author keywords

Carbohydrates; Electrophilic substitution; Glycals; Nucleophilic substitution; Palladium; Umpolung

Indexed keywords

EID: 70349194905     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200900585     Document Type: Article

References (144)

1. M. H. D. Postema, J. L. Piper, R. L. Betts, Synlett 2005, 1345-1358.
2. a) E. C. K. Lai, S. A. Morris, I. P. Street, S. G. Withers, Bioorg. Med. Chem. 1996, 4, 1929-1937;
3. b) J. Yu, L. C. Hsieh, L. Kochersperger, S. Yonkovich, J. C. Stephans, M. A. Gallop, P. G. Schultz, Angew. Chem. Int. Ed. Engl. 1994, 33, 339-341.
4. a) R. J. Ferrier, J. O. Hoberg, Adv. Carbohydr. Chem. Biochem. 2003, 58, 55-119;
5. b) R. J. Ferrier, O.A. Zubkov, Org. React. 2003, 62, 569-736;
6. c) R. J.Ferrier, in: Topics in Current Chemistry, Springer-Verlag, Berlin, 2001, vol.215, pp. 153-175;
7. d) L. Somsák, Chem. Rev. 2001, 101, 81-135;
8. e) W Priebe, G. Grynkiewicz, in: Glycoscience: Chemistry and Chemical Biology, Springer, Heidelberg, 2001;
9. f) B. Fraser-Reid, Ace. Chem. Res. 1985, 18, 347-354;
10. g) B. Fraser-Reid, Ace. Chem. Res. 1975, 8, 192-201;
11. h) R.J. Ferrier, Adv. Carbohydr. Chem. Biochem. 1970, 24, 199-266.
12. a) X. Yuan, R. J. Linhardt, Curr. Top. Med. Chem. 2005, 5, 1393-1430;
13. b) T. Skrydstrup, B. Vauzeilles, J. M. Beau, in: Glycoscience: Chemistry and Chemical Biology (Eds.: B. Fraser Reid, K. Tatstuta, J. Thiem), Springer, Heidelberg, 2001, vol.3, p. 2679;
14. c) T. Skrydstrup, B. Vauzeilles, J-M. Beau, in: Carbohydrates in Chemistry and Biology. The Chemistry of Saccharides (Eds.: B. Ernst, G. W Hart, P. Sinaý), Wiley-VCH, New York, 2000, vol.1, chapter 20;
15. d) H. Togo, W. He, Y. Waki, M. Yokohama, Synlett 1998, 700-717;
16. e) Y. Du, R. J.Linhardt, I. R. Vlahov,' Tetrahedron 1998, 54, 9913-9959;
17. f) M. H. D. Postema, in: C-Glycoside Synthesis, CRC Press, Boca Raton, FL, 1995;
18. g) J-M. Beau, T. Gallaher, Top. Curr. Chem. 1997, 187, 1-54;
19. h) M. H. D. Postema, Tetrahedron 1992, 48, 8545-8599.
20. Aryl C-glycosides: a) T Bililign, B. R. Griffith, J. S. Thorson, Nat. Prod. Rep. 2005, 22, 742-760;
21. b) C. Jaramillo, S. Knappe Synthesis 1994, 1-20;
22. c) K. Suzuki, Pure Appl. Chem. 1994, 66, 2175-2178.
23. J-M. Beau, T. Gallagher, Top. Curr. Chem, 1997, 187, 1-54.
24. K. C. Nicolaou, C.-K. Hwang, M. E. Duggan, J. Chem. Soc, Chem. Commun. 1986, 925-926.
25. S. Hanessian, M. Martin, R. C. Desai, J. Chem. Soc, Chem. Commun. 1986, 926-927.
26. P. LeSimple, J-M. Beau, G Jaurand, P. Sinaý, Tetrahedron Lett. 1986, 27, 6201-6204.
27. J. R. Bearder, M. L. Dewis, D. A. Whiting, J. Chem. Soc. Perkin Trans. 1 1995, 227-233.
28. T. Mochizuki, M. Shiozaki, Chem. Lett. 1997, 26, 801-802.
29. J. Prandi, C. Audin, J-M. Beau, Tetrahedron Lett. 1991, 32, 769-772.
30. a) K. A. Parker, D.-S. Su, J. Org. Chem. 1996, 61, 2191-2194;
31. b) K. A. Parker, Y.-h. Koh, C. A. Coburn, J. Org. Chem. 1995, 60, 2938-2941;
32. c) K. A. Parker, Y.-h. Koh, J. Am. Chem. Soc. 1994, 116, 11149-11150;
33. d) K. A. Parker, Pure Appl. Chem. 1994, 66, 2135-2138;
34. e) K. A. Parker, C.A. Coburn, P.D. Johnson, P. Aristoff, J. Org. Chem. 1992, 57, 5547-5550;
35. f) K. A. Parker, C.A. Coburn, J. Am. Chem. Soc. 1991, 113, 8516-8518.
36. a) K. H. Dötz, F. Otto, M. Nieger, J. Organomet. Chem. 2001, 621, 77-88;
37. b) K. H. Dötz, R. Ehlenz, D. Paetsch, Angew. Chem. Int. Ed. Engl. 1997, 36, 2376-2378.
38. Review: R.W. Friesen, J.Chem. Soc. Perkin Trans. 1 2001, 1969-2001.
39. R. W Friesen, C. F. Sturino, A. K. Daljeet, A. Kolaczewska, J. Org. Chem. 1991, 56, 1944-1947.
40. a) R. R. Schmidt, R. Preuss, R. Betz, Tetrahedron Lett. 1987, 28, 6591-6594;
41. b) R. Preuss, R. R. Schmidt, Liebigs Ann. Chem. 1989, 429-434;
42. c) R. R. Schmidt, R. Preuss, Tetrahedron Lett. 1989, 30, 3409-3412;
43. d) S. Maier, R. Preuss, R. R. Schmidt, Liebigs Ann. Chem. 1990, 483-489;
44. e) R. R. Schmidt, H. Dietrich, Angew. Chem. Int. Ed. Engl. 1991, 30, 1328-1329;
45. f) R. R. Schmidt, A. Beyerbach, Liebigs Ann. Chem. 1992, 983-986;
46. g) K. Frische, R. R. Schmidt, Liebigs Ann. Chem. 1994, 297-303;
47. h) H. Dietrich, R. R. Schmidt, Liebigs Ann. Chem. 1994, 975-981;
48. i) T. Eisele, H. Ishida, G. Hummel, R. R. Schmidt, Liebigs Ann. 1995, 2113-2121;
49. j) B. Patro, R. R. Schmidt, J. Carbohydr. Chem. 2000, 19, 817-826.
50. For related systems, see: a) E. Boyd, R. V. H. Jones, P. Quayle, A. J.Waring (née Potts), Tetrahedron Lett. 2006, 47, 7983-7986 (Scheme 1, a, X = F);
51. b) E. Boyd, M. R. Hallett, R. V. H. Jones, J. E. Painter, P. Patel, P. Quayle, A. J.Waring (née Potts), Tetrahedron Lett. 2006, 47, 8337-8341 (Scheme 1, a, X = Cl).
52. Review: S. Jarosz, A. Zamojski, Curr. Org. Chem. 2003, 7, 121.
53. K. Jarowicki, C.Kilner, P. J.Kocienski, Z. Komsta, J. E. Milne, A. Wojtasiewicz, V. Coombs, Synthesis 2008, 2747-2763, and references therein.
54. J. C. Conway, C. J. Urch, P. Quayle, J. Xu, Synlett 2006, 776-780.
55. Coupling of C-I stannyl glycals: a) P. Steunenberg, V. Jeanneret, Y.-H. Zhu, P. Vogel, Tetrahedron: Asymmetry 2005, 16, 337-346;
56. b) A. Abas, R. L. Beddoes, J. C. Conway, P. Quayle, C. J. Urch, Synlett 1995, 1264-1266;
57. c) E. Dubois, JM. Beau, J. Chem. Soc, Chem. Commun. 1990, 1191-1192;
58. d) E. Dubois, J.-M. Beau, Carbohydr. Res. 1992, 228, 103-120;
59. e) R. W. Friesen, C. F. Sturino, J. Org. Chem. 1990, 55, 2572-2574.
60. Coupling of C-I iodo glycals: a) C.-L. Chen, S. F. Martin, J. Org. Chem. 2006, 71, 4810-4817;
61. b) C.-L. Chen, S. F. Martin, Org. Lett. 2004, 6, 3581-3584;
62. c) J. S. Potuzak, D. S. Tan, Tetrahedron Lett. 2004, 45, 1797-1802;
63. d) D. E. Kaelin, O. D. Lopez, S. F. Martin,.J. Am. Chem. Soc. 2001, 123, 6937-6938;
64. e) M. A. Brimble, H. S. Chan, Aust. J. Chem. 1998, 51, 235-242;
65. f) R. W. Friesen, R. W Loo, C. F. Sturino, Can. J. Chem. 1994, 72, 1262-1272;
66. g) R. W Friesen, R.W. Loo, J. Org. Chem. 1991, 56, 4821-4823.
67. H. C. Zhang, M. Brakta, G. D. Daves Jr., Tetrahedron Lett. 1993, 34, 1571-1574.
68. a) M. H. D. Postema, D. Calimente, J. Org. Chem. 1999, 64, 1770-1771;
69. b) M. H. D. Postema, D. Calimente, Tetrahedron Lett. 1999, 40, 4755-4759;
70. c) M. H. D. Postema, D. Calimente, L. Liu, T. L. Behrmann, J. Org. Chem. 2000, 65, 6061-6068;
71. d) L. Liu, M. H. D. Postema, J. Am. Chem. Soc. 2001, 123, 8602-8603;
72. e) M. H. D. Postema, J.L. Piper, Org. Lett. 2003, 5, 1721-1723;
73. f) M. H. D. Postema, J. L. Piper, L. Liu, J. Shen, M. Faust, P. Andreana, J. Org. Chem. 2003, 68, 4748-4754;
74. g) M. H. D. Postema, J. L. Piper, V. Komanduri, L. Liu, Angew. Chem. Int. Ed. 2004, 43, 2915-2918;
75. h) J. L. Piper, M. H. D. Postema, J. Org. Chem. 2004, 69, 7395-7398;
76. i) M. R. Chaulagain, M. H. D. Postema, F. Valeriote, H. Pietraszkewicz, Tetrahedron Lett. 2004, 45, 7791-7794;
77. j) M. H. D. Postema, J. L. Piper, R. L. Betts, F. A. Valeriote, H. Pietraszkewicz, J. Org. Chem. 2005, 70, 829-836.
78. K. Iyer, J. D. Rainier, J. Am. Chem. Soc. 2007, 129, 12604-12605.
79. a) H. Fuwa, M. Sasaki, Org. Lett. 2008, 10, 2549-2552;
80. b) H. Fuwa, S. Naito, T. Goto, M. Sasaki, Angew. Chem. Int. Ed. 2008, 47, 4737-4739.
81. K. F.W. Hekking, M. A. H. Moelands, F.L. Van Delft, F. P. J. T. Rutjes, J. Org. Chem. 2006, 71, 6444-6450.
82. A related approach based on RCM has been described: B. Schmidt, A. Biernat, Chem. Eur. J. 2008, 14, 6135-6141.
83. a) N. Khan, X. Cheng, D. R. Mootoo, J. Am. Chem. Soc. 1999, 121, 4918-4919;
84. b) X. Cheng, N. Khan, D. R. Mootoo, J. Org. Chem. 2000, 65, 2544-2547;
85. c) K. A. Tony, R. W Denton, A. Dilhas, J.Jiménez-Barbero, D. R. Mootoo, Org. Lett. 2007, 9, 1441-1444;
86. d) R. W Denton, K. A. Tony, J. J.Hernández-Gay, F. J. Cañada, J.Jiménez-Barbero, D. R. Mootoo, Carbohydr. Res. 2007, 342, 1624-1635.
87. J. Mlynarski, A. Banaszek, Carbohydr. Res. 1996, 295, 69-75.
88. a) J.G. Buchanan, A. P. W Clelland, T. Johnson, R. A. C. Rennie, R. H. Whightman, J. Chem. Soc. Perkin Trans. 1 1992, 2593-2601;
89. b) S. H. Mahmoud, L. Somsák, I. Parkas, Carbohydr. Res. 1994, 254, 91-104;
90. c) L. Somsák, Carbohydr. Res. 1996, 286, 167-171.
91. a) P. Meindl, H. Tuppy, Monatsh. Chem. 1969, 100, 1295-1306;
92. b) K. Okamoto, T. Kondo, T. Goto, Bull. Chem. Soc. Jpn. 1987, 60, 631-636;
93. cj K. Ikeda, K. Konishi, K. Sano, K. Tanaka, Chem. Pharm. Bull. 2000, 48, 163-165;
94. d) M. D. Burkart, S. P. Vincent, C.-H. Wong, Chem. Commun. 1999, 1525-1526;
95. e) E. J. Horn, J. Gervay-Hague, J. Org. Chem. 2009, 74, 4357-4359.
96. M. von Itzstein, R. J. Thompson, Curr. Med. Chem. 1997, 4, 185-210.
97. T. Angata, A. Varki, Chem. Rev. 2002, 102, 439-469.
98. X.-L. Sun, Y. Kanie, C.-T. Guo, O. Kanie, Y. Suzuki, C.-H. Wong, Ew. J. Org. Chem. 2000, 2642-2653.
99. Miscellaneous methods for the preparation of C-I glycals: a) L. Somsák, I. Bajza, G. Batta, Liebigs Ann. Chem. 1990, 1265-1268;
100. b) F.E. McDonald, H. Y. H. Zhu, C.R. Holmquist, J.Am. Chem. Soc. 1995, 117, 6605-6606;
101. c) M. R. Hallett, J.E. Painter, P. Quayle, D. Ricketts, Tetrahedron Lett. 1998, 39, 2851-2852;
102. d) S. R. Pulley, J. P. Carey, J. Org. Chem. 1998, 63, 5275-5279;
103. e) T. Vidal, A. Haudrechy, Y. Langlois, Tetrahedron Lett. 1999, 40, 5677-5680;
104. f) V. Popsavin, O. Beric, O. M. Popsavin, L. Radie, J. Csanadi, V. Cirin-Novta, Tetrahedron 2000, 56, 5929-5940.
105. A. M. Gómez, M. Casillas, S. Valverde, J. C. López, Chem. Commun. 1996, 2357-2358.
106. a) A. M. Gómez, A. Pedregosa, M. Casillas, C. Uriel, J. C. López, Eur. J. Org. Chem. 2009, 3579-3588;
107. b) S.-C. Hung, C.H. Wong, Tetrahedron Lett. 1996, 37, 4903-4906;
108. c) B. Ernst, T. Winkler, Tetrahedron Lett. 1989, 30, 3081-3084.
109. For a related approach see: S. Harusawa, M. Kawabata, Y. Murai, R. Yoneda, T. Kurihara, Chem. Pharm. Bull. 1995, 43, 152-155.
110. Review: C. Taillefumier, Y. Chapleur, Chem. Rev. 2004, 104, 263-292.
111. a) A. M. Gómez, A. Pedregosa, S. Valverde, J. C. López, Chem. Commun. 2002, 2022-2023;
112. b) A. M. Gómez, A. Barrio, A.Pedregosa, S. Valverde, J. C. López, Tetrahedron Lett. 2003, 44, 8433-8435.
113. J. Tsuji, Tetrahedron 1986, 42, 4261-4401.
114. a) J. Tsuji, H. Kataoka, Y. Kobayashi, Tetrahedron Lett. 1981, 22, 2575-2578;
115. b) B. M. Trost, G. A. Molander, J. Am. Chem. Soc. 1981, 103, 5969-5972.
116. B. M. Trost, D. L. Van Kranken, Chem. Rev. 1996, 96, 395-422.
117. O. Fujiwara, K. Takai, K. Utimoto, J. Org. Chem. 1990, 55, 1705-1706.
118. Y. Masuyama, J. Nakata, Y Kuru.su, J. Chem. Soc. Perkin Trans. 1 1991, 2598-2599.'
119. J. M. Aurrecoechea, E. Iztueta, 'Tetrahedron Lett. 1995, 36, 7129-7132.
120. a) S. Araki, K. Kameda, J. Tanaka, T. Hirashita, H. Yamamura, M. Kawai, J. Org. Chem. 2001, 66, 7919-7921;
121. b) S. Araki, T. Kamei, T. Hirashita, H. Yamamura, M. Kawai, Org. Lett. 2000, 2, 847-849;
122. c) T. Tabuchi, J. Inanaga, M. Yamaguchi, Tetrahedron Lett. 1986, 27, 1195-1196.
123. Review: Y. Tamaru, Eur. J. Org. Chem. 2005, 2647-2656, and references therein.
124. P. Girard, J. L. Namy, H. B. Kagan, J. Am. Chem. Soc. 1980, 102, 2693-2698.
125. a) T. Tabuchi, J.Inanaga, M. Yamaguchi, Tetrahedron Lett. 1986, 27, 3891-3894;
126. b) A. Krief, A. M. Laval, Chem. Rev. 1999, 99, 745-777.
127. M. Kimura, M. Shimizu, K. Shibata, M. T'azoe, Y. Tamaru, Angew. Chem. Int. Ed. 2003, 42, 3392-3395.
128. However, vinyloxiran.es had been made to react with carbonyl compounds by indium/palladium-mediated allylation: S. Araki, K. Kameda, J. Tanaka, T. Hirashita, H. Yamamura, M. Kawai, J. Org. Chem. 2001, 66, 7919-7921.
129. J. A. Marshall, Chem. Rev. 2000, 100, 3163-3186.
130. M. Beller, C. BoIm, in: Transition metals for organic synthesis: building blocks and fine chemicals, Wiley, Weinheim, 2004.
131. N. Ogumi, T. Omi, Tetrahedron Lett, 1984, 25, 2823-2824.
132. 3N (1..... 3%).
133. Two hemiacetals - 2,3:5,6-di-O-isopropylidene-D-mannofur-anose and 2,3:4,6-di-0-isopropylidene-D-mannopyranose -were also subjected to the same reaction conditions with compound 6, but failed to give any coupled products.
134. a) A. M. Echavarren, D. R. Tueting, J. K. Stille, J. Am. Chem. Soc. 1988, 110, 4039-4041;
135. b) D. R. Tueting, A. M. Echavarren, J. K. Stille, Tetrahedron 1989, 45, 979-992.
136. a) A. M. Castaño, M. Ruano, A. M. Echavarren, Tetrahedron Lett. 1996, 37, 6591-6594;
137. b) A. M. Castaño, M. Méndez, M. Ruano, A. M. Echavarren, J. Org. Chem. 2001, 66, 589-593.
138. a) K. Nozaki, K. Oshima, K. Utimoto, J. Am. Chem. Soc. 1987, 109, 2547-2549;
139. b) K. Nozaki, K. Oshima, K. Utimoto, Tetrahedron 1989, 45, 923-933.
140. A. M. Gómez, J. C. López, B. Fraser-Reid, J. Chem. Soc. Perkin Trans. 1 1994, 1689-1695.
141. A. W. Mazur, G.D. Hiler II, J. Org. Chem. 1997, 62, 4471-4475.
142. A. M. Gómez, M. D. Company, S. Valverde, J. C. López, Org. ' Lett. 2002, 4, 383-386.
143. P. Ruchet, J.-M. Vatele, J. Gore, Synthesis 1994, 795-799.
144. H. Galons, I. Bergerat, C. Combet-Famoux, M. Miocque, G. Decodts, G. Bram, J. Chem. Soc, Chem. Commun. 1985, 1730-1731.