Total syntheses of conformationally locked difluorinated pentopyranose analogues and a pentopyranosyl phosphate mimetic

Journal of Organic Chemistry

Volumn 72, Issue 5, 2007, Pages 1575-1587

  Miles, Jonathan A L ^a   Mitchell, Lisa ^a,b   Percy, Jonathan M ^b   Singh, Kuldip ^a   Uneyama, E ^a  

^a UNIVERSITY OF LEICESTER   (United Kingdom)

^b UNIVERSITY OF STRATHCLYDE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

DIHYDROXYLATION; GLYCOSYL PHOSPHATE; TRANSANNULAR HEMIACETALIZATION;

ALCOHOLS; CONFORMATIONS; EPOXIDATION; PHOSPHATES; SYNTHESIS (CHEMICAL);

AROMATIC COMPOUNDS;

ALCOHOL DERIVATIVE; ALLYL COMPOUND; BICYCLO COMPOUND; DIFLUOROENOL; GLYCOSYL PHOSPHATE; PENTOPYRANOSE DERIVATIVE; PENTOPYRANOSYL PHOSPHATE; PYRAN DERIVATIVE; TRIFLUOROETHANOL; UNCLASSIFIED DRUG;

ACETALIZATION; ARTICLE; CONFORMATION; DIHYDROXYLATION; EPOXIDATION; FLUORINATION; RING OPENING; SYNTHESIS; WITTIG REACTION; WITTIG REARRANGEMENT;

CRYSTALLOGRAPHY, X-RAY; HETEROCYCLIC COMPOUNDS, 2-RING; HYDROCARBONS, FLUORINATED; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR MIMICRY; OXIDATION-REDUCTION; QUATERNARY AMMONIUM COMPOUNDS;

EID: 33847618281     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0620258     Document Type: Article

References (101)

1. (a) Loganathan, D.; Aich, U. Glycobiology 2006, 16, 343.
2. (b) Laederach, A.; Reilly, P. J. Proteins: Struct., Funct., Bioinf. 2005, 60, 591.
3. (c) Carcabal, P.; Jockusch, R. A.; Hunig, I.; Snoek, L. C.; Kroemer, R. T.; Davis, B. G.; Gamblin, D. P.; Compagnon, I.; Oomens, J.; Simons, J. P. J. Am. Chem. Soc. 2005, 127, 11414.
4. (d) Flint, J.; Bolam, D. N.; Nurizzo, D.; Taylor, E. J.; Williamson, M. P.; Walters, C.; Davies, G. J.; Gilbert, H. J. J. Biol. Chem. 2005, 280, 23718.
5. (e) Fernandez, M. D.; Canada, F. J.; Jimenez-Barbero, J.; Cuevas, G. J. Am. Chem. Soc. 2005, 127, 7379.
6. (f) Mitchell, E. P.; Sabin, C.; Snajdrova, L.; Pokorna, M.; Perret, S.; Gautier, C.; Hofr, C.; Gilboa-Garber, N.; Koca, J.; Wimmerova, M.; Imberty, A. Proteins: Struct., Funct., Bioinf. 2005, 58, 735.
7. (g) Loris, R.; Imberty, A.; Beeckmans, S.; Van, Driessche, E.; Read, J. S.; Bouckaertt, J.; De Greve, H.; Buts, L.; Wyns, L. J. Biol. Chem. 2003, 278, 16297.
8. (h) Vyas, N. K.; Vyas, M. N.; Chervenak, M. C.; Bundle, D. R.; Pinto, B. M.; Quiocho, F. A. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 15023.
9. (i) Pathiaseril, A.; Woods, R. J. J. Am. Chem. Soc. 2000, 122, 331.
10. (j) Zacharias, M.; Straatsma, T. P.; McCammon, J. A.; Quiocho, F. A. Biochemistry 1993, 32, 7428.
11. (k) Quiocho, F. A. Biochem. Soc. Trans. 1993, 21, 442.
12. (l) Jimenez-Barbero, J.; Canada, F. J.; Cuevas, G.; Asensio, J. L.; Aboitiz, N.; Canales, A.; Chavez, M. I.; Fernandez-Alonso, M. C.; Garcia-Herrero, A.; Mari, S.; Vidai, P. NMR Spectroscopy and Computer Modeling of Carbohydrates: Recent Advances; ACS Symposium Series 930; American Chemical Society: Washington, DC. 2006; p 60.
13. (m) Bryce, R. A.; Millier, I. H.; Naismith, J. H. Biophys. J. 2001, 81, 1373.
14. (a) Kirby, A. The Anomeric Effect and Related Stereoelectronic Effects at Oxygen; Springer-Verlag: Berlin, 1983.
15. (b) For recent mechanistic studies, see: Bennet, A. J.; Kitos, T. E. J. Chem. Soc., Perkin Trans. 2002, 2, 1207.
16. (c) For a computational examination of the mechanism, see: Dimelow, R. J.; Bryce, R. A.; Masters, A. J.; Hillier, I. H.; Burton, N. A. J. Chem. Phys. 2006, 124.
17. (d) Mohr, M.; Bryce, R. A.; Hillier, I. H. J. Phys. Chem. A 2001, 105, 8216.
18. (a) Haneda, T.; Goekjian, P. G.; Kim, S. H.; Kishi, Y. J. Org. Chem. 1992, 57, 490.
19. (b) Goekjian, P. G.; Wu, T. C.; Kang, H. Y.; Kishi, Y. J. Org. Chem. 1991, 56, 6422.
20. (c) Kuntz, D. A.; Ghavami, A.; Johnston, B. D.; Pinto, B. M.; Rose, D. R. Tetrahedron: Asymmetry 2005, 16, 25.
21. (d) Yang, G. L.; Schmieg, J.; Tsuji, M.; Franck, R. W. Angew. Chem., Int. Ed. 2004, 43, 3818.
22. (e) Mikkelsen, L. M.; Hernaiz, M. J.; Martin-Pastor, M.; Skrydstrup, T.; Jimenez-Barbero, J. J. Am. Chem. Soc. 2002, 124, 14940.
23. For reviews, see: (f) Sears, P.; Wong, C. H. Angew. Chem., Int. Ed. 1999, 38, 2301.
24. (g) Wong, C. H. Acc. Chem. Res. 1999, 32, 376.
25. (a) Wang, W.; Zhang, Y. M.; Sollogoub, M.; Sinay, P. Angew. Chem., Int. Ed. 2000, 39, 2466.
26. (b) Wang, W.; Zhang, Y. M.; Zhou, H. H.; Bleriot, Y.; Sinay, P. Eur. J. Org. Chem. 2001, 1053.
27. Paquette, L. A.; Zhang, Y. L. J. Org. Chem. 2006, 71, 4353.
28. (a) Mehta, G.; Pallavi, K. Tetrahedron Lett. 2004, 45, 3865.
29. (b) Mehta, G.; Pallavi, K. Chem. Commun. 2002, 2828.
30. (c) For a review of earlier work, see: Mehta, G.; Singh, V. Chem. Rev. 1999, 99, 881.
31. van Hooft, P. A. V.; Litjens, R.; van der Marel, G. A.; van Boeckel, C. A. A.; van Boom, J. H. Org. Lett. 2001, 3, 731.
32. Briggs, A. J.; Evans, C. M.; Glenn, R.; Kirby, A. J. J. Chem. Soc., Perkin Trans. 2 1983, 1637.
33. For recent examples, see: (a) Bleriot, Y.; Vadivel, S. K.; Herrera, A. J.; Greig, I. R.; Kirby, A. J.; Sinay, P. Tetrahedron 2004, 60, 6813.
34. (b) Lorthiois, E.; Meyyappan, M.; Vasella, A. Chem. Commun. 2000, 1829.
35. (a) Audouard, C.; Fawcett, J.; Griffiths, G. A.; Percy, J. M.; Pintat, S.; Smith, C. A. Org. Biomol. Chem. 2004, 2, 528.
36. (b) Audouard, C.; Fawcett, J.; Griffith, G. A.; Kerouredan, E.; Miah, A.; Percy, J. M.; Yang, H. L. Org. Lett. 2004, 6, 4269.
37. (c) Kariuki, B. M.; Owton, W. M.; Percy, J. M.; Pintat, S.; Smith, C. A.; Spencer, N. S.; Thomas, A. C.; Watson, M. Chem. Commun. 2002, 228.
38. (d) Butt, A. H.; Percy, J. M.; Spencer, N. S. Chem. Commun. 2000, 1691.
39. (a) Fustero, S.; Catalan, S.; Piera, J.; Sanz-Cervera, J. F.; Fernandez, B.; Acena, J. L. J. Org. Chem. 2006, 71, 4010.
40. (b) Fustero, S.; Sanchez-Rosello, M.; Jimenez, D.; Sanz-Cervera, J. F.; del Pozo, C.; Acena, J. L. J. Org. Chem. 2006, 71, 2706.
41. (c) Fustero, S.; Bartolome, A.; Sanz-Cervera, J. F.; Sanchez-Rosello, M.; Soler, J. G.; de Arellano, C. R.; Fuentes, A. S. Org. Lett. 2003, 5, 2523.
42. (d) Yang, Y. Y.; Meng, W. D.; Qing, F. L. Org. Lett. 2004, 6, 4257.
43. (e) You, Z. W.; Wu, Y. Y.; Qing, F. L. Tetrahedron Lett. 2004, 45, 9479.
44. (f) De Matteis, V.; van Delft, F. L.; de Gelder, R.; Tiebes, J.; Rutjes, F. Tetrahedron Lett. 2004, 45, 959.
45. (g) Marhold, M.; Buer, A.; Hiemstra, H.; van Maarseveen, J. H.; Haufe, G. Tetrahedron Lett. 2004, 45, 57.
46. Thibaudeau, C.; Plavec, J.; Chattopadhyaya, J. J. Org. Chem. 1998, 63, 4967.
47. Griffith, G. A.; Percy, J. M.; Pintat, S.; Smith, C. A.; Spencer, N.; Uneyama, E. Org. Biomol. Chem. 2005, 3, 2701.
48. Fawcett, J.; Griffiths, G. A.; Percy, J. M.; Pintat, S.; Smith, C. A.; Spencer, N.; Uneyama, E. Chem. Commun. 2004, 302.
49. Fawcett, J.; Griffith, G. A.; Percy, J. M.; Uneyama, E. Org. Lett. 2004, 6, 1277.
50. Yamana, M.; Ishihara, T.; Ando, T. Tetrahedron Lett. 1983, 24, 507.
51. (a) Amii, H.; Kobayashi, T.; Hatamoto, Y.; Uneyama, K. Chem. Commun. 1999, 1323.
52. (h) For a review, see: Uneyama, K.; Amii, H. J. Fluorine Chem. 2002, 114, 127.
53. Kuroboshi, M.; Ishihara, T. Bull. Chem. Soc. Jpn. 1990, 63, 428.
54. Felix, C.; Laurent, A.; Mison, P. J. Fluorine Chem. 1995, 70, 71.
55. Griffith, G. A.; Hillier, I. H.; Percy, J. M.; Roig, R.; Vincent, M. A. J. Org. Chem. 2006, 71, 8250.
56. Patel, S. T.; Percy, J. M.; Wilkes, R. D. Tetrahedron 1995, 51, 9201.
57. Patel, S. T.; Percy, J. M.; Wilkes, R. D. J. Org. Chem. 1996, 61, 166.
58. Broadhurst, M. J.; Brown, S. J.; Percy, J. M.; Prime, M. E. J. Chem. Soc., Perkin Trans. 1 2000, 3217.
59. For general reviews of RCM issues, see: (a) Conrad, J. C.; Fogg, D. E. Curr. Org. Chem. 2006, 10, 185.
60. (b) Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem., Int. Ed. 2005, 44, 4490.
61. (e) Furstner, A. Angew. Chem., Int. Ed. 2000, 39, 3013.
62. For reviews of medium ring forming RCM, see: (a) Deiters, A.; Martin, S. F. Chem. Rev. 2004, 104, 2199.
63. (b) Maier, M. E. Angew. Chem., Int. Ed. 2000, 39, 2073.
64. (c) Yet, L. Chem. Rev. 2000, 100, 2963.
65. (d) Michaut, A.; Rodriguez, J. Angew. Chem., Int. Ed. 2006, 45, 5740.
66. For recent examples, see: (e) Bleriot, Y.; Giroult, A.; Mallet, J. M.; Rodriguez, E.; Vogel, P.; Sinay, P. Tetrahedron: Asymmetry 2002, 13, 2553.
67. (f) Bourgeois, D.; Mahuteau, J.; Pancrazi, A.; Nolan, S. P.; Prunet, J. Synthesis 2000, 869.
68. (g) Boyer, F. D.; Hanna, I.; Nolan, S. P. J. Org. Chem. 2001, 66, 4094.
69. (h) Buono, F.; Tenaglia, A. J. Org. Chem. 2000, 65, 3869.
70. (i) Furstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 8746.
71. (j) Buszek, K. R.; Sato, N.; Jeong, Y. Tetrahedron Lett. 2002, 43, 181.
72. Illuminati, G.; Mandolini, L. Acc. Chem. Res. 1981, 14, 95.
73. Furstner, A.; Guth, O.; Duffels, A.; Seidel, G.; Liebl, M.; Gabor, B.; Mynott, R. Chem.-Eur. J. 2001, 7, 4811.
74. (a) Creighton and co-workers identified an open-chain dimer by LC-MS from a mixture of products generated during a cyclooctannulation reaction: Creighton, C. J.; Du, Y. M.; Reitz, A. B. Bioorg. Med. Chem. 2004, 12, 4375.
75. For recent applications, see: (b) Creighton, C. J.; Du, Y. M.; Santulli, R. J.; Tounge, B. A.; Reitz, A. B. Bioorg. Med. Chem. Lett. 2006, 16, 3971.
76. (c) Abell, A. D.; Brown, K. M.; Coxon, J. M.; Jones, M. A.; Miyamoto, S.; Neffe, A. T.; Nikkel, J. M.; Stuart, B. G. Peptides 2005, 26, 251.
77. Santford, M. S.; Love, J. A.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 6543.
78. Chatterjee, A. K.; Choi, T. L.; Sanders, D. P.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 11360.
79. (a) Kingsbury, J. S.; Harrity, J. P. A.; Bonitatebus, P. J.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 791.
80. (b) For a review, see: Hoveyda, A. H.; Gillingham, D. G.; Van Veldhuizen, J. J.; Kataoka, O.; Garber, S. B.; Kingsbury, J. S.; Harrity, J. P. A. Org. Biomol. Chem. 2004, 2, 8.
81. Yang, D.; Wong, M.-K.; Yip, Y.-C. J. Org. Chem. 1995, 60, 3887.
82. For examples of related oxidations, see: (a) Csuk, R.; Dorr, P. Tetrahedron 1994, 50, 9983.
83. (b) Angibeaud, P.; Defaye, J.; Gadelle, A.; Utille, J. P. Synthesis 1985, 1123.
84. (c) Hayes, C. J.; Sherlock, A. E.; Selby, M. D. Org. Biomol. Chem. 2006, 4, 193.
85. (d) Ochiai, M.; Ito, T.; Takahashi, H.; Nakanishi, A.; Toyonari, M.; Sueda, T.; Goto, S.; Shiro, M. J. Am. Chem. Soc. 1996, 118, 7716.
86. (e) Arnone, A.; Bernardi. R.; Cavicchioli, M.; Resnati, G. J. Org. Chem. 1995, 60, 2314.
87. Cicala, G.; Curci, R.; Fiorentino, M.; Laricchiuta, O. J. Org. Chem. 1982,47, 2670.
88. White, J. D.; Hrnciar, P. J. Org. Chem. 2000, 65, 9129.
89. Eliel, E. L.; Wilen, S. H.; Mander, L. N. Stereochemistry of Organic Compounds: Wiley-Interscience: New York. 1994; p 769.
90. Gelb, M. H.; Svaren, J. P.; Abeles, R. H. Biochemistry 1985, 24, 1813.
91. (a) For a computational study of the prototypical transannular reaction, see: Parveen; Singh, H.; Singh, T. V.; Bharatam, P. V.; Venugopalan, P. Theochem: J. Mol. Struct. 2004, 685, 139.
92. For a recent elegant synthetic application of a transannular reaction, see: (b) Nicolaou, K. C.; Carenzi, G. E. A.; Jeso, V. Angew. Chem., Int. Ed. 2005, 44, 3895.
93. (c) Park, C. M. J. Org. Chem. 2006, 71, 413.
94. VanRheenen, V.; Kelly, R. C.; Cha, D. Y. Tetrahedron Lett. 1976, 1973.
95. Donohoe, T. J. Synlett 2002, 1223.
96. Donohoe, T. J.; Johnson, P. D.; Pye, R. J.; Keenan, M. Org. Lett. 2005, 7, 1275. This paper describes a well-characterized cyclic osmate ester complexed to TMEDA.
97. Tiwari, P.; Misra, A. K. J. Org. Chem. 2006, 71, 2911.
98. Spartan 04, version 1.0.3, Wavefunction Inc.: 18401 Von Karman Avenue, Suite 370, Irvine. CA 92612, 2005
99. a units lower than those of the analogous alcohols), see: Guthrie, J. P.; Pitchko, V. J. Am. Chem. Soc. 2000, 122, 5520.
100. a units: Jencks, W. P. Catalysis in Chemistry and Enzymology, McGraw-Hill: New York, 1969: p 522.
101. N of 0.5). This may explain the relatively low selectivity.