Stereoselective synthesis of C-ketosides by sequential intramolecular hydrogen atom transfer-intermolecular allylation reaction

Tetrahedron Letters

Volumn 49, Issue 35, 2008, Pages 5179-5181

  Martín, Angeles ^a   Pérez Martín, Inés ^a   Quintanal, Luis M ^a   Suárez, Ernesto ^a  

^a INSTITUTO DE PRODUCTOS NATURALES Y AGROBIOLOGÍA   (Spain)

Author keywords

Allylation; C Ketoside; Hydrogen transfer; Radical reaction; Tandem

Indexed keywords

ALLYL COMPOUND; ALLYLTRI N BUTYLTIN; C KETOSIDE DERIVATIVE; GLYCOSIDE; HYDROGEN; PHTHALIMIDE DERIVATIVE;

ALLYLATION; ARTICLE; CHEMICAL STRUCTURE; ISOMERISM; MOLECULAR INTERACTION; RADICAL REACTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 47049116768     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.06.070     Document Type: Article

References (95)

1. Baytas S.N., Wang Q., Karst N.A., Dordick J.S., and Linhardt R.J. J. Org. Chem. 69 (2004) 6900-6903
2. Ohnishi Y., and Ichikawa Y. Bioorg. Med. Chem. Lett. 12 (2002) 997-999
3. Khodair A.I., and Schmidt R.R. Carbohydr. Res. 337 (2002) 1967-1978
4. Dondoni A., Giovannini P.P., and Marra A. J. Chem. Soc., Perkin Trans. 1 19 (2001) 2380-2388
5. Dondoni A., Mariotti G., Marra A., and Massi A. Synthesis 14 (2001) 2129-2137
6. Notz W., Hartel C., Waldscheck B., and Schmidt R.R. J. Org. Chem. 66 (2001) 4250-4260
7. Poveda A., Asensio J.L., Polat T., Bazin H., Linhardt R.J., and Jimenez-Barbero J. Eur. J. Org. Chem. (2000) 1805-1814
8. Wang Q., Wolff M., Polat T., Du Y., and Linhardt R.J. Bioorg. Med. Chem. Lett. 10 (2000) 941-944
9. Koketsu M., Kuberan B., and Linhardt R.J. Org. Lett. 2 (2000) 3361-3363
10. Bazin H.G., Du Y., Polat T., and Linhardt R.J. J. Org. Chem. 64 (1999) 7254-7259
11. Kuribayashi T., Mizuno Y., Gohya S., and Satoh S. J. Carbohydr. Chem. 18 (1999) 371-382
12. Dondoni A., and Marra A. Chem. Commun. 16 (1998) 1741-1742
13. Du Y., Polat T., and Linhardt R.J. Tetrahedron Lett. 39 (1998) 5007-5010
14. Du Y., and Linhardt R.J. Carbohydr. Res. 308 (1998) 161-164
15. Wallimann K., and Vasella A. Helv. Chim. Acta 74 (1991) 1520-1532
16. Crich D., and Lim L.B.L. Tetrahedron Lett. 31 (1990) 1897-1900
17. For reviews on natural products, see for example:. Nakata T. Chem. Rev. 105 (2005) 4314-4347
18. Yasumoto T., and Murata M. Chem. Rev. 93 (1993) 1897-1909
19. For the synthesis of C-ketosides as chiral synthons, see:. Johnson H.W.B., Majumder U., and Rainier J.D. J. Am. Chem. Soc. 127 (2005) 848-849
20. Allwein S.P., Cox J.M., Howard B.E., Johnson H.W.B., and Rainier J.D. Tetrahedron 58 (2002) 1997-2009
21. Nicolaou K.C., Bunnage M.E., McGarry D.G., Shi S., Somers P.K., Wallace P.A., Chu X.-J., Agrios K.A., Gunzner J.L., and Yang Z. Chem. Eur. J. 5 (1999) 599-617
22. Oishi T., Naguno Y., and Hirama M. Chem. Commun. (1998) 1041-1042
23. Suh H., and Wilcox C.S. J. Am. Chem. Soc. 110 (1988) 470-481
24. For a detailed list of procedures to generate C-ketosides prior to 2004, see:. Roberts S.W., and Rainier J.D. Org. Lett. 7 (2005) 1141-1144
25. For more recent references, see:. Herrera A.J., Rondon M., and Suarez E. Synlett (2007) 1851-1856
26. Malapelle A., Coslovi A., Doisneau G., and Beau J.M. Eur. J. Org. Chem. (2007) 3145-3157
27. Gomez A.M., Uriel C., Valverde S., and Lopez J.C. Org. Lett. 8 (2006) 3187-3190
28. Majumder U., Cox J.M., Johnson H.W.B., and Rainier J.D. Chem. Eur. J. 12 (2006) 1736-1746
29. Schweizer F., and Hindsgaul O. Carbohydr. Res. 341 (2006) 1730-1736
30. Zhang K.D., and Schweizer F. Synlett (2005) 3111-3115
31. Lavrenov S.N., Solovyeva N.P., Reznikova M.I., Anisimova O.S., and Preobrazhenskaya M.N. Nucleosides, Nucleotides Nucleic Acids 23 (2004) 281-289
32. Reviews on C-glycosides:. Wellington K.W., and Benner S.A. Nucleosides Nucleotides Nucleic Acids 25 (2006) 1309-1333
33. Bililign T., Griffith B.R., and Thorson J.S. Nat. Prod. Rep. 22 (2005) 742-760
34. Lee D.Y.W., and He M.S. Curr. Top. Med. Chem. 5 (2005) 1333-1350
35. Dondoni A., and Marra A. Chem. Rev. 100 (2000) 4395-4421
36. Vogel P., Ferritto R., Kraehenbuehl K., and Baudat A. In: Chapleur Y. (Ed). Carbohydrate Mimics: Concepts and Methods (1998), Chemie, Weinheim Chapter 2, pp 19-48
37. Togo H., He W., Waki Y., and Yokoyama M. Synlett (1998) 700-717
38. Du Y.G., Linhardt R.J., and Vlahov I.R. Tetrahedron 54 (1998) 9913-9959
39. Beau J.M., and Gallagher T. Top. Curr. Chem. 187 (1997) 1-54
40. Nicotra F. Top. Curr. Chem. 187 (1997) 55-83
41. Levy D.E., and Tang C. The Chemistry of C-Glycosides (1995), Elsevier, Cambridge
42. Postema M.H.D. Tetrahedron 48 (1992) 8545-8599
43. Giese B., Dupuis J., Leising M., Nix M., and Lindner H.J. Carbohydr. Res. 171 (1987) 329-341
44. Dupuis J., Giese B., Hartung J., Leising M., Korth H.-G., and Sustmann R. J. Am. Chem. Soc. 107 (1985) 4332-4333
45. Chen G.-R., Fei Z.B., Huang X.-T., Xie Y.-Y., Xu J.-L., Gola J., Steng M., and Pral J.-P. Eur. J. Org. Chem (2001) 2939-2946
46. Wang Q., and Linhardt R.J. J. Org. Chem. 68 (2003) 2668-2672
47. Polat T., Du Y., and Linhardt R.J. Synlett (1998) 1195-1196
48. Vlahov I.R., Vlahov P.I., and Linhardt R.J. J. Am. Chem. Soc. 119 (1997) 1480-1481
49. Paulsen H., and Matschulat P. Liebigs Ann. Chem. (1991) 487-495
50. Nagy J.O., and Bernadsky M.D. Tetrahedron Lett. 32 (1991) 3953-3956
51. Beckwith A.L.J., and Duggan P.J. Tetrahedron 54 (1998) 4623-4632
52. Beckwith A.L.J., and Duggan P.J. Tetrahedron 54 (1998) 6919-6928
53. Curran D.P., Porter N.A., and Giese B. Stereochemistry of Radical Reactions (1995), VCH, Weinheim
54. Giese B. Angew. Chem., Int. Ed. Engl. 28 (1989) 969-980
55. Korth H.-G., Sustmann R., Dupuis J., and Giese B. J. Chem. Soc., Perkin Trans. 2 (1986) 1453-1459
56. Barton D.H.R., Hartwig W., and Motherwell W.B. J. Chem. Soc., Chem. Commun. (1982) 4397-4410
57. Cekovic Z. J. Serb. Chem. Soc. 70 (2005) 287-318
58. Feray L., Kuznetsov N., and Renaud P. In: Renaud P., and Sibi M.P. (Eds). Radicals in Organic Synthesis Vol. 2 (2001), Wiley-VCH, Weinheim 246-278
59. Robertson J., Pillai J., and Lush R.K. Chem. Soc. Rev. 30 (2001) 94-103
60. Majetich G. Tetrahedron 51 (1995) 7095-7129
61. Dorigo A.E., McCarrick M.A., Loncharich R.J., and Houk K.N. J. Am. Chem. Soc. 112 (1990) 7508-7514
62. Dorigo A.E., and Houk K.N. J. Am. Chem. Soc. 109 (1987) 2195-2197
63. Dorta R.L., Martín A., Salazar J.A., Suárez E., and Prangé T. J. Org. Chem. 63 (1998) 2251-2261
64. Martín A., Salazar J.A., and Suárez E. J. Org. Chem. 61 (1996) 3999-4006
65. Danishefsky S.J., Armistead D.M., Wincott F.E., Selnick H.G., and Hungate R. J. Am. Chem. Soc. 109 (1987) 8117-8119
66. Kay I.T., and Bartholomew D. Tetrahedron Lett. 25 (1984) 2035-2038
67. Concepción J.I., Francisco C.G., Hernández R., Salazar J.A., and Suárez E. Tetrahedron Lett. 25 (1984) 1953-1956
68. Brun P., and Waegell B. In: Abramovitch R.A. (Ed). Reactive Intermediates Vol. 3 (1983), Plenum Press, New York 367-426
69. Petrovic G., and Cekovic Z. Synthesis (2004) 1671-1679
70. Petrovic G., and Cekovic Z. Org. Lett. 2 (2000) 3769-3772
71. Petrovic G., and Cekovic Z. Tetrahedron 55 (1999) 1377-1390
72. Petrovic G., and Cekovic Z. Tetrahedron Lett. 38 (1997) 627-630
73. Cekovic Z., and Ilijev D. Tetrahedron Lett. 29 (1988) 1441-1444
74. For a review on oxygen-centered radicals, see:. Hartung J., Gottwald T., and Spehar K. Synthesis (2002) 1469-1498
75. Kim S., Lee T.A., and Song Y. Synlett (1998) 471-472
76. Okada K., Okamoto K., and Oda M. J. Am. Chem. Soc. 110 (1988) 8736-8738
77. Okada K., Okamoto K., and Oda M. J. Chem. Soc., Chem. Commun. (1989) 1636-1637
78. Barton D.H.R., Blundell P., and Jaszberenyi J.Cs. Tetrahedron Lett. 30 (1989) 2341-2344
79. Crich D., Huang X., and Newcomb M. J. Org. Chem. 65 (2000) 523-529
80. Crich D., Huang X., and Newcomb M. Org. Lett. 1 (1999) 225-227
81. Mitsunobu O. Synthesis (1981) 1-28
82. Grochowski E., and Jurczak J. Synthesis (1976) 682-684
83. A similar moderate yield was obtained in the related addition of glucopyranosyl radical to acrylonitrile:. Giese B., Dupuis J., and Nix M. Org. Synth. 65 (1987) 236-242
84. The methoxy group at C-5 can be easily distinguished by 2D-HSQC and HMBC correlations.
85. Praly J.-P. Tetrahedron Lett. 24 (1983) 3075-3078
86. Giese B., and Dupuis J. Tetrahedron Lett. 25 (1984) 1349-1352
87. Brunckova J., Crich D., and Yao Q. Tetrahedron Lett. 35 (1994) 6619-6622
88. Yamazaki N., Eichenberger E., and Curran D.P. Tetrahedron Lett. 35 (1994) 6623-6626
89. Crich D., Sun S., and Brunckova J. J. Org. Chem. 61 (1996) 605-615
90. Hayday K., and McKelvey R.D. J. Org. Chem. 41 (1976) 2222-2226
91. Beckwith A.L.J., and Easton C.J. J. Am. Chem. Soc. 103 (1981) 615-619
92. Beckwith A.L.J., and Brumby S. J. Chem. Soc., Perkin Trans. 2 (1987) 1801-1807
93. Martín A., Quintanal L.M., and Suárez E. Tetrahedron Lett. 48 (2007) 5507-5511
94. Araki Y., Endo T., Tanji M., Nagasawa J., and Ishido Y. Tetrahedron Lett. 29 (1988) 351-354
95. A word of caution should be given in regard to the C-4 stereochemistry of 8 and 10. The chromatographic separation of these diastereoisomeric mixtures proved impossible even after derivatization of the primary alcohol. In consequence, the C-4 stereochemistry has only been tentatively assigned on the basis of NOESY experiments of the major isomer in the mixture spectra. Nevertheless, the results shown in Table 1 are consistent with the steric effects previously observed for furanosyl radical additions, see Refs. 8c, 8d, 21.