'Traceless' solid-phase synthesis of furans via 1,3-dipolar cycloaddition reactions of isomunchnones

Tetrahedron Letters

Volumn 38, Issue 40, 1997, Pages 6973-6976

  Gowravaram, Madhusudhan R ^a,b   Gallop, Mark A ^a  

^a AFFYMAX RESEARCH INSTITUTE   (United States)

^b ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

FURAN DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; TECHNIQUE;

EID: 0030817243     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01667-5     Document Type: Article

References (37)

1. (a) Balkenhohl, F.; von dem Bussche-Hunnefeld, C.; Lansky, A.; Zechel, C. Angew. Chem. Int. Ed. Engl. 1996, 35, 2288.
2. (b) Gordon, E. M.; Gallop, M. A.; Patel, D. V. Acc. Chem. Res. 1996, 29, 144.
3. (c) Terrett, N. K.; Gardner, M.; Gordon, D. W.; Kobylecki, R. J.; Steele, J. Tetrahedron 1995, 51, 8135.
4. (a) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1996, 52, 4527.
5. (b) ibid, 1997, 53, 5643.
6. (c) Nefzi, A.; Ostresh, J. M.; Houghten, R. A. Chem. Rev. 1997, 97, 449.
7. (d) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555.
8. (e) Fruchtel, J. S.; Jung, G. Angew. Chem. Int. Ed. Engl. 1996, 35, 17.
9. For some recent examples, see (a) Pop, I. E.; Deprez, B. P.; Tartar, A. L. J. Org. Chem. 1997, 62, 2594.
10. (b) Kobayashi, S.; Nagayama, S. J. Am. Chem. Soc. 1996, 118, 8977.
11. (c) Liu, Y.; Vederas, J. C. J. Org. Chem. 1996, 61, 7856.
12. (d) Bolm, C.; Gerlach, A. Angew. Chem. Int. Ed. Engl. 1997, 36, 741.
13. (e) Kaldor, S. W.; Siegel, M. G.; Fritz, J. E.; Dressman, B. A.; Hahn, P. J. Tetrahedron Lett. 1996, 37, 7193.
14. (a) Studer, A.; Jeger, P.; Wipf, P.; Curran, D. P. J. Org. Chem. 1997, 62, 2917.
15. (b) Studer, A.; Hadida, S.; Ferritto, R.; Kim, S.-Y.; Jeger, P.; Wipf, P.; Curran, D. P. Science, 1997, 275, 823.
16. (c) Curran, D. P.; Hoshino, M. J. Org. Chem. 1996, 61, 6480.
17. (a) Marino, Jr. J. P.; Osterhout, M. H.; Padwa, A. J. Org. Chem. 1995, 60, 2704.
18. (b) Ye, T.; McKerey, M. A. Chem. Rev. 1994, 94, 1091.
19. (c) Padwa, A.; Hertzog, D. L.; Nadler, W. R.; Osterhout, M. H.; Price, A. T. J. Org. Chem. 1994, 59, 1418.
20. (d) Padwa, A.; Hertzog, D. L. Tetrahedron 1993, 49, 2589.
21. (e) Padwa, A.; Hertzog, D. L.; Chinn, R. L. Tetrahedron Lett. 1989, 30, 4077.
22. The design of "traceless" linkers for solid-phase organic synthesis has attracted considerable recent interest. E.g. see, (a) Brown, A. R.; Rees, D. C.; Rankovic, Z.; Morphy, J. R. J. Am. Chem. Soc. 1997, 119, 3288.
23. (b) Gayo, L. M.; Suto, M. J. Tetrahedron Lett. 1997, 38, 211.
24. (c) Zhao, X.-y.; Jung, K. W.; Janda, K. D. Tetrahedron Lett. 1997, 38, 977.
25. (d) Plunkett, M. J.; Ellman, J. A. J. Org. Chem. 1997, 62, 2885.
26. (e) Boehm, T. L.; Showalter, H. D. H. J. Org. Chem. 1996, 61, 6498.
27. (f) Han, Y.; Walker, S. D.; Young, R. N. Tetrahedron Lett. 1996, 37, 2703.
28. (g) Chenera, B.; Finkelstein, J. A.; Veber, D. F. J. Am. Chem. Soc. 1995, 117, 11999.
29. (h) Lorsbach, B. A.; Miller, R. B.; Kurth, M. J. J. Org. Chem. 1996, 63, 8716.
30. Solid-phase syntheses of pyrroles, employing related cycloaddition reactions of münchnones to alkynes, have recently been described; see: (a) Strocker, A. M.; Keating, T. A.; Tempest, P. A.; Armstrong, R. W. Tetrahedron Lett. 1996, 37, 1149.
31. (b) Mjalli, A. M. M.; Sarshar, S.; Baiga, T. J. Tetrahedron Lett. 1996, 37, 2943.
32. (c) Keating, T. A.; Armstrong, R. W. J. Am. Chem. Soc. 1996, 118, 2574.
33. 2 resin (purchased from Rapp Polymere, Tubingen, Germany) does not contain secondary amide bonds in the polymer/linker backbone and hence is a suitable support for selective imide synthesis.
34. 19C resonances for the labeled methyl group in amide (6d), imide (7d) and diazoimide (8d) appear at 23.3, 25.9 and 24.2 ppm respectively. For a detailed description of the gel-phase NMR method, see Look, G. C.; Holmes, C. P.; Chinn, J. P.; Gallop, M. A. J. Org. Chem. 1994, 59, 7588.
35. All products gave satisfactory proton NMR, and HRMS spectra.
36. Note that the requirement for using electron-deficient alkynes in this cydoaddition chemistry does significantly restrict access to a wider range of structurally diverse furan libraries.
37. 4.