Isoxazoline-carbocyclic aminols for nucleoside synthesis through aza-Diels-Alder reactions

Tetrahedron

Volumn 62, Issue 31, 2006, Pages 7370-7379

  Quadrelli, Paolo ^a   Piccanello, Andrea ^a   Martinez, Naiara Vazquez ^a   Bovio, Bruna ^a   Mella, Mariella ^a   Caramella, Pierluigi ^a  

^a UNIVERSITY OF PAVIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOCYCLIC NUCLEOSIDE; CYCLOPENTADIENE DERIVATIVE; HETEROCYCLIC COMPOUND; HYDROXYL GROUP; ISOXAZOLINE DERIVATIVE; NITRIC OXIDE; NORBORNENE DERIVATIVE;

AMINO ACID SYNTHESIS; ARTICLE; CHEMICAL STRUCTURE; CYCLOADDITION; DIELS ALDER REACTION; DRUG SYNTHESIS; PRIORITY JOURNAL;

BETULACEAE;

EID: 33745198672     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.05.029     Document Type: Article

References (76)

1. Mizuno Y. The Organic Chemistry of Nucleic Acids (1986), Kadansha, Tokyo
2. Ueda T. In: Townsend (Ed). Chemistry of Nucleosides and Nucleotides Vol. 1 (1988), Plenum, New York, NY Chapter 1
3. Srivasta P.C., Robins R.K., and Meyer Jr. R.B. In: Townsend (Ed). Chemistry of Nucleosides and Nucleotides Vol. 1 (1988), Plenum, New York, NY Chapter 2
4. Revenkar G.R., and Robins R.K. In: Townsend (Ed). Chemistry of Nucleosides and Nucleotides Vol. 2 (1988), Plenum, New York, NY Chapter 4
5. Merino P. Curr. Med. Chem.: Anti-Infect. Agents 1 (2002) 389-411
6. Crimmins M.T. Tetrahedron 54 (1998) 9229-9272
7. Agrofoglio L., Suhas E., Farese A., Condom R., Challand S.R., Earl R.A., and Guedj R. Tetrahedron 50 (1994) 10611-10670
8. Kitade Y., Kojima H., Zulfiqur F., Kim H.S., and Wataya Y. Bioorg. Med. Chem. Lett. 13 (2003) 3963-3965
9. Ramesh N.G., Klunder A.J.H., and Zwanenburg B. J. Org. Chem. 64 (1999) 3635-3641
10. Wu J., Schneller S.W., Seley K.L., and DeClerq E. Heterocycles 47 (1998) 757-763
11. Siddiqi S.M., Raissian M., Schneller S.W., Ikeda S., Snoeck R., Andrei G., Balzarini J., and DeClerq E. Bioorg. Med. Chem. Lett. 3 (1993) 663-666
12. Da Silva A.D., Coimbra E.S., Fourrey J.L., Machado A.S., and Robert-Gero M. Tetrahedron Lett. 34 (1993) 6745-6748
13. Koga M., and Schneller S.W. Tetrahedron Lett. 31 (1990) 5861-5864
14. Quadrelli P., Scrocchi R., Caramella P., Rescifina A., and Piperno A. Tetrahedron 60 (2004) 3643-3651
15. Kirby G.W. Chem. Soc. Rev. 6 (1977) 1-24
16. Vogt P.F., and Miller M.J. Tetrahedron 54 (1998) 1317-1348
17. Boger L., and Weinreb S.M. Hetero Diels-Alder Methodology in Organic Synthesis (1987), Academic, San Diego, CA
18. Quadrelli P., Gamba Invernizzi A., and Caramella P. Tetrahedron Lett. 37 (1996) 1909-1996
19. Quadrelli P., Mella M., Gamba Invernizzi A., and Caramella P. Tetrahedron 55 (1999) 10497-10510
20. Quadrelli P., Mella M., Paganoni P., and Caramella P. Eur. J. Org. Chem. (2000) 2613-2620
21. Quadrelli P., Fassardi V., Cardarelli A., and Caramella P. Eur. J. Org. Chem. (2002) 2058-2065
22. Borthwick A.D., and Biggadike K. Tetrahedron 48 (1992) 571-623
23. Archelos A., and Morin C. Tetrahedron Lett. 25 (1984) 1277-1278
24. Daluge S., and Vince R. J. Org. Chem. 43 (1978) 2311-2320
25. Jagt J.C., and van Leusen A.M. J. Org. Chem. 39 (1974) 564-566
26. Ishikura M., and Katagiri N. Recent Research Developments in Organic Chemistry 8 (2004) 197-205
27. Ishikura M., and Katagiri N. Trends Heterocycl. Chem. 9 (2003) 83-90
28. Ruecroft G., and Taylor S. Chem. Br. 38 (2002) 46-49
29. Griffiths G.J., and Previdoli F.E. J. Org. Chem. 58 (1993) 6129-6131
30. For an example of pricing see: Aldrich Handbook, ed. 2005-2006, p 249.
31. Grieco P.A., and Bahsas A. J. Org. Chem. 52 (1987) 5746-5749
32. Larsen S.D., and Grieco P.A. J. Am. Chem. Soc. 107 (1985) 1768-1769
33. Rodriguez-Borges J.E., Garcia-Mera X., Fernandez F., Lopes V.H.C., Magalhaes A.L., and Cordeiro M.N.D.S. Tetrahedron 61 (2005) 10951-10957
34. Grieco P.A., Parker D.T., Fobare W.F., and Ruckle R. J. Am. Chem. Soc. 109 (1987) 5859-5861
35. Grieco P.A., Larsen S.D., and Fobare W.F. Tetrahedron Lett. 27 (1986) 1975-1978
36. Alonso D.A., Bertilsson S.K., Johnsson S.Y., Nordin S.J.M., Södergren M.J., and Andersson P.G. J. Org. Chem. 64 (1999) 2276-2280
37. Bailey P.D., Wilson R.D., and Brown G.R. Tetrahedron Lett. 30 (1989) 6781-6784
38. Waldman H. Angew. Chem., Int. Ed. Engl. 27 (1988) 274-275
39. Abraham H., and Stella L. Tetrahedron 48 (1992) 9707-9718
40. Stella L., and Abraham H. Tetrahedron Lett. 31 (1990) 2603-2606
41. Grieco P.A., and Larsen S.D. Org. Synth. 68 (1990) 206-209
42. Caramella P., and Grünager P. In: Padwa A. (Ed). 1,3-Dipolar Cycloaddition Chemistry Vol. 1 (1984), Wiley, New York, NY 291-392
43. Fliege W., and Huisgen R. Justus Liebigs Ann. Chem. (1973) 2038-2047
44. Yu L., Li J., Ramirez J., Chen D., and Weng P.G. J. Org. Chem. 62 (1997) 903-907
45. Pinho P., and Andersson P.G. Chem. Commun. (1999) 597-598
46. Huisgen R., Ooms P.H.J., Mingin M., and Allinger N.L. J. Am. Chem. Soc. 102 (1980) 3951-3953
47. Rondan N.G., Paddon-Row M.N., Caramella P., and Houk K.N. J. Am. Chem. Soc. 103 (1981) 2436-2438
48. Caramella P., Rondan N.G., Paddon-Row M.N., and Houk K.N. J. Am. Chem. Soc. 103 (1981) 2438-2440
49. Houk K.N., Rondan N.G., Brown F.K., Jorgensen W.L., Madura J.D., and Spellmeyer D.C. J. Am. Chem. Soc. 105 (1983) 5980-5988
50. Eliel E.L., and Wilen S.H. Stereochemistry of Organic Compounds (1994), Wiley, New York, NY pp 627-628
51. Bonin M., Romero J.R., Grierson D.S., and Huson H.P. J. Org. Chem. 49 (1984) 2392-2400
52. Ferrer M., Sanchez-Baeza F., and Messeguer A. Tetrahedron 53 (1997) 15877-15888
53. Bergstad K., and Bäckvall J.E. J. Org. Chem. 63 (1998) 6650-6655
54. Choudary B.M., Bharathi B., Venkat Reddy C., Lakshmi Kantam M., and Raghavan K.V. Chem. Commun. (2001) 1736
55. Buston J.E.H., Coldham I., and Mulholland K.R. J. Chem. Soc., Perkin Trans. 1 (1999) 2327
56. Grierson D.S., and Husson H.P. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis Vol. 6 (1991), Pergamon, Oxford 909-947
57. Michelot R. Bull. Soc. Chim. Fr. (1969) 4377-4385
58. Lebrun B., Braekman J.C., and Daloze D. Magn. Reson. Chem. 37 (1999) 60-64 and references therein
59. Parham W.E., Sloan K.B., Ratnammal Reddy K., and Olson P.E. J. Org. Chem. 38 (1973) 927-931
60. 3-3,5-dimethylpyrazole as suggested by literature for similar compounds failed and the starting N-acetyl derivatives were collected unchanged after application of various reaction conditions. For some examples see:
61. Blay G., Cardona L., Garcia B., Garcia C.L., and Pedro J.R. Tetrahedron Lett. 38 (1997) 8257-8260
62. Corey E.J., and Fleet G.W.J. Tetrahedron Lett. (1973) 4499-4501
63. Salmond W.G., Barta M.A., and Havens J.L. J. Org. Chem. 43 (1978) 2057-2059
64. Doering W.V.E., Levitz M., Sayigh A., Sprecher M., and Whelan W.P. J. Am. Chem. Soc. 75 (1953) 1008
65. Zhu X.-F., Nydegger F., and Gossauer A. Helv. Chim. Acta 87 (2004) 2245-2265
66. Gershtein N.A., and Shostakoskii M.F. Zh. Obshch. Khim. 18 (1948) 451-458
67. Shostakoskii M.F., and Gershtein N.A. Zh. Obshch. Khim. 16 (1946) 937-951
68. Schultz, Forrest S. Book of Abstracts, 218th ACS National Meeting, New Orleans, LA, Aug 22-26, 1999.
69. Shimizu, H.; Saito, N.; Matsuzawa, K.; Aizawa, S. Jpn. Kokai Tokkyo Koho JP 07069955, 1995.
70. Domenicano A., Vaciago A., and Coulson C.A. Acta Crystallogr., Sect. B 31 (1975) 221-234
71. Cremer D., and Pople J.A. J. Am. Chem. Soc. 97 (1975) 1354-1358
72. Cahn R.S., Ingold C.K., and Prelog V. Experientia 12 (1956) 81-94
73. Grundmann C., and Grünanger P. The Nitrile Oxide (1971), Springer, Heidelberg
74. Wilson A.J.C. Nature 150 (1942) 151-152
75. Sheldrick G.M. SHELXL-93. Program for the Refinement of Crystal Structures (1993), University of Göttingen, Germany
76. Johnson C.K. ORTEP, Report ORNL-3793 (1965), Oak Ridge National Laboratory, Oak Ridge, TN