Intramolecular 1,5-hydrogen atom transfer reaction promoted by phosphoramidyl and carbamoyl radicals: synthesis of 2-amino-C-glycosides

Tetrahedron Letters

Volumn 48, Issue 36, 2007, Pages 6384-6388

  Francisco, Cosme G ^a   Herrera, Antonio J ^a   Martín, Ángeles ^a   Pérez Martín, Inés ^a   Suárez, Ernesto ^a  

^a INSTITUTO DE PRODUCTOS NATURALES Y AGROBIOLOGÍA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

2H FURO[3,2 B]PYRROLE; CARBAMOYL RADICAL; GLYCOSIDE; HYDROGEN; IODINE; LEWIS ACID; OCTAHYDROPYRANO[3,2 B]PYRROLE; PHOSPHORAMIDYL RADICAL; PYRROLE; RADICAL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; DEPROTECTION REACTION; GLYCOSIDATION; HYDROLYSIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEAR OVERHAUSER EFFECT; OXIDATION; OZONOLYSIS; REDUCTION; SYNTHESIS; TEMPERATURE DEPENDENCE;

EID: 34547691252     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.06.152     Document Type: Article

References (76)

1. Recent reviews:. 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
2. Robertson J., Pillai J., and Lush R.K. Chem. Soc. Rev. 30 (2001) 94-103
3. Majetich G., and Wheless K. Tetrahedron 51 (1995) 7095-7129
4. For recent reviews on the chemistry of nitrogen-centered radicals see:. Stella L. In: Renaud P., and Sibi M.P. (Eds). Radicals in Organic Synthesis Vol. 2 (2001), Wiley-VCH, Weinheim 407-426
5. Fallis A.G., and Brinza I.M. Tetrahedron 53 (1997) 17543-17594
6. Zard S.Z. Synlett (1996) 1148-1155
7. Esker J.L., and Newcomb M. In: Katritzky A.R. (Ed). Advances in Heterocyclic Chemistry Vol. 58 (1993), Academic Press, New York 1-45
8. Stella L. Angew. Chem., Int. Ed. Engl. 22 (1983) 337-350
9. For previous reviews, see:. Mackiewicz P., and Furstoss R. Tetrahedron 34 (1978) 3241-3260
10. Neale R.S. Synthesis (1971) 1-15
11. For a recent review on the synthesis of heterocycles by radical cyclization see:. Bowman W.R., Bridge C.F., and Brookes P. J. Chem. Soc., Perkin Trans. 1 (2000) 1-14
12. Hofmann A.W. Ber. 16 (1883) 558-560
13. Loëffler K., and Freytag C. Ber. 42 (1909) 3427-3431
14. Barton D.H.R., Beckwith A.L.J., and Goosen A. J. Chem. Soc. (1965) 181-190
15. Baldwin J.E., Barton D.H.R., Dainis I., and Pereira J.L.C. J. Chem. Soc. (1968) 2283-2289
16. Carruthers W. Some Modern Methods of Organic Synthesis. 2nd ed. (1978), Cambridge University Press, Cambridge pp 255-257
17. Gagosz F., Moutrille C., and Zard S.Z. Org. Lett. 4 (2002) 2707-2709
18. Lin X., Stien D., and Weinreb S.M. Tetrahedron Lett. 41 (2000) 2333-2337
19. Clark A.J., Filik R.P., Peacock J.L., and Thomas G.H. Synlett (1999) 441-443
20. Clark A.J., Deeth R.J., Samuel C.J., and Wongtap H. Synlett (1999) 444-446
21. Esker J.L., and Newcomb M. J. Org. Chem. 59 (1994) 2779-2786
22. Esker J.L., and Newcomb M. Tetrahedron Lett. 34 (1993) 6877-6880
23. Esker J.L., and Newcomb M. J. Org. Chem. 58 (1993) 4933-4940
24. Martín A., Pérez-Martín I., and Suárez E. Org. Lett. 7 (2005) 2027-2030
25. Francisco C.G., Herrera A.J., and Suárez E. J. Org. Chem. 68 (2003) 1012-1017
26. Freire R., Martín A., Pérez-Martín I., and Suárez E. Tetrahedron Lett. 43 (2002) 5113-5116
27. Dorta R.L., Francisco C.G., and Suárez E. J. Chem. Soc., Chem. Commun. (1989) 1168-1169
28. Armas P., Francisco C.G., Hernández R., Salazar J.A., and Suárez E. J. Chem. Soc., Perkin Trans. 1 (1988) 3255-3265
29. Carrau R., Hernández R., Suárez E., and Betancor C. J. Chem. Soc., Perkin Trans. 1 (1987) 937-943
30. Bililign T., Griffith B.R., and Thorson J.S. Nat. Prod. Rep. 22 (2005) 742-760
31. Dondoni A., and Marra A. Chem. Rev. 100 (2000) 4395-4421
32. Vogel P., Ferritto K.K., and Baudat A. In: Chapleur Y. (Ed). Carbohydrate Mimics: Concepts and Methods (1998), Verlag Chemie, Weinheim 19-48 Chapter 2
33. Togo H., He W., Waki Y., and Yokoyama M. Synlett (1998) 700-717
34. Du Y.G., Linhardt R.J., and Vlahov I.R. Tetrahedron 54 (1998) 9913-9959
35. Beau J.M., and Gallagher T. Top. Curr. Chem. 187 (1997) 1-54
36. Nicotra F. Top. Curr. Chem. 187 (1997) 55-83
37. Levy D.E., and Tang C. The Chemistry of C-Glycosides (1995), Elsevier, Cambridge
38. Postema M.H.D. Tetrahedron 48 (1992) 8545-8599
39. Röhrig C.H., Takhi M., and Schmidt R.R. Synlett (2001) 1170-1172
40. Dondoni A., Mariotti G., and Marra A. Tetrahedron Lett. 41 (2000) 3483-3486
41. Fuchss T., and Schmidt R.R. Synthesis (1998) 753-758
42. Urban D., Skrydstrup T., and Beau J.-M. Chem. Commun. (1998) 955-956
43. Burkhart F., Hoffmann M., and Kessler H. Angew. Chem., Int. Ed. Engl. 36 (1997) 1191-1192
44. Wang L.-X., Fan J.-Q., and Lee Y.C. Tetrahedron Lett. 37 (1996) 1975-1978
45. For earlier methods for the synthesis of 2-amino-C-glycosides see:. Grant L., Walsh K.E., Walter D.S., and Gallagher T. Org. Lett. 4 (2002) 4623-4625 and references cited herein
46. SanMartin R., Tavassoli B., Walsh K.E., Walter D.S., and Gallagher T. Org. Lett. 2 (2000) 4051-4054 and references cited herein
47. For more recent methods, see:. Wen X.H., and Hultin P.G. Tetrahedron Lett. 45 (2004) 1773-1775
48. Liu Y., and Gallagher T. Org. Lett. 6 (2004) 2445-2448
49. Miquel N., Vignando S., Russo G., and Lay L. Synlett (2004) 341-343
50. McGarvey G.J., Schmidtmann F.W., Benedum T.E., and Kizer D.E. Tetrahedron Lett. 44 (2003) 3775-3779
51. Palmier S., Vauzeilles B., and Beau J.M. Org. Biomol. Chem. 1 (2003) 1097-1098
52. Gaurat O., Xie J., and Valery J.M. J. Carbohydr. Chem. 22 (2003) 645-656
53. Xie J. Carbohydr. Res. 338 (2003) 399-406
54. Pachamuthu K., Gupta A., Das J., Schmidt R.R., and Vankar Y.D. Eur. J. Org. Chem. (2002) 1479-1483
55. Ohnishi Y., and Ichikawa Y. Bioorg. Med. Chem. Lett. 12 (2002) 997-999
56. Dondoni A., Mariotti G., and Marra A. J. Org. Chem. 67 (2002) 4475-4486
57. For the synthesis of other octahydropyrano [3,2-b]pyrrole carbohydrate related structures see:. Jayakanthan K., and Vankar Y.D. Tetrahedron Lett. 47 (2006) 8667-8671
58. Nie X., and Wang G. J. Org. Chem. 70 (2005) 8687-8692
59. Streicher B., and Wünsch B. Eur. J. Org. Chem. (2001) 115-120
60. Cipolla L., Lay L., and Nicotra F. J. Org. Chem. 62 (1997) 6678-6681
61. Saito K.-I., Sugai K., Fujikura K., Yamada N., Goto M., Ban C., Hayasaka E., Sugiyama N., and Tomita K. Carbohydr. Res. 185 (1989) 307-314
62. Richter P.K., Tomaszewski M.J., Miller R.A., Patron A.P., and Nicolaou K.C. J. Chem. Soc., Chem. Commun. (1994) 1151-1152
63. Luengo J.I., and Gleason J.G. Tetrahedron Lett. 33 (1992) 6911-6914
64. Giannis A., and Sandhoff K. Tetrahedron Lett. 26 (1985) 1479-1482
65. Although not frequently used as a protecting group for amines, the diphenoxyphosphoryl group can also be removed under mild conditions. For an example in carbohydrate chemistry, see:. Wolfrom M.L., Conigliaro P.J., and Soltes E.J. J. Org. Chem. 32 (1967) 653-655
66. Zervas L., and Konstas S. Ber. 93 (1960) 435-446
67. Francisco C.G., Freire R., Herrera A.J., Pérez-Martín I., and Suárez E. Org. Lett. 4 (2002) 1959-1961
68. Dorta R.L., Martín A., Prangé T., Salazar J.A., and Suárez E. J. Org. Chem. 63 (1998) 2251-2261
69. Dorta R.L., Martín A., Prangé T., and Suárez E. Tetrahedron: Asymmetry 7 (1996) 1907-1910
70. Martín A., Salazar J.A., and Suárez E. J. Org. Chem. 61 (1996) 3999-4006
71. Dorta R.L., Martín A., Salazar J.A., Suárez E., and Prangé T. Tetrahedron Lett. 37 (1996) 6021-6024
72. Hernández R., Medina M.C., Salazar J.A., Suárez E., and Prangé T. Tetrahedron Lett. 28 (1987) 2533-2536
73. Kimura M., and Ban Y. Synthesis (1976) 201-202
74. For related hemiaminal-enamine rearrangements, see:. Ge C.S., Hourcade S., Ferdenzi A., Chiaroni A., Mons S., Delpech B., and Marazano C. Eur. J. Org. Chem. (2006) 4106-4114
75. Carroll F.I., Chaudhari S., Thomas J.B., Mascarella S.W., Gigstad K.M., Deschamps J., and Navarro H.A. J. Med. Chem. 48 (2005) 8182-8193
76. Thiering S., Sowa C.E., and Thiem J. J. Chem. Soc., Perkin Trans. 1 (2001) 801-806