Simple synthesis of 5-substituted resorcinols: A revisited family of interesting bioactive molecules

Journal of Organic Chemistry

Volumn 62, Issue 2, 1997, Pages 417-421

  Alonso, Emma ^a   Ramón, Diego J ^a   Yus, Miguel ^a  

^a UNIVERSITY OF ALICANTE   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

BENZYL ALCOHOL DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; REACTION ANALYSIS;

EID: 0031053263     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9610624     Document Type: Article

References (51)

1. See, for instance: Brown, G. D. J. Nat. Prod. 1992, 55, 1756.
2. Lindenberg, B. A.; Massin, M. J. Physiol. (Paris) 1957, 49, 285.
3. Wasser, C.; Silva, F.; Rodríguez, E. Experientia 1990, 46, 500.
4. Lytollis, W.; Scannell, R. T.; An, H.; Murty, V. S.; Reddy, K. S.; Barr, J. R.; Hecht, S. M. J. Am. Chem. Soc. 1995, 117, 12683.
5. For a review on cannabis, see: Mechoulam, R.; McCallum, N. K.; Burstein, S. Chem. Rev. 1976, 76, 75.
6. See, for instance: Baek, S.-H.; Srebnik, M.; Mechoulam, R. Tetrahedron Lett. 1985, 26, 1083.
7. Mannila, E.; Talvitie, A. Liebigs Ann. Chem. 1993, 1037.
8. Thakkar, K.; Geahlen, R. L.; Cushman, M. J. Med. Chem. 1993, 36, 2950.
9. (a) Yus, M.; Ramón, D. J. J. Chem. Soc., Chem. Commun. 1991, 5398.
10. (b) For a review, see: Yus, M. Chem. Soc. Rev. 1996, 155.
11. (c) For the last paper on an arene-catalyzed lithiation from our laboratory, see: Almena, J.; Foubelo, F.; Yus, M. J. Org. Chem. 1996, 61, 1859.
12. Naphthalene or 4,4′-di-tert-butylbiphenyl (DTBB) are the most usual arene as electron transfer catalysts. For a comparative study on the use of both arenes, see: Freeman, P. K.; Hutchinson, L. L. J. Org. Chem. 1980, 45, 1924.
13. Alonso, E.; Guijarro, D.; Yus, M. Tetrahedron 1995, 51, 11457.
14. Conventional methods involving halogen-lithium interchange are not useful for the preparation of allylic or benzylic lithium reagents due to the almost exclusive formation of Wurtz-type products, (a) See, for instance: Wakefield, B. J. Organolithium Methods; Academic Press: London, 1988; p 38.
15. (b) For an alternative method using allylic or benzylic mesylates, see: Guijarro, D.; Mancheño, B.; Yus, M. Tetrahedron 1992, 48, 4593.
16. 13g see, for example: (a) Marmor, R. S. J. Org. Chem. 1972, 37, 2901. (b) Foucla, A.; Teitel, S.; Prossi, A. J. Org. Chem. 1977, 42, 3456. Stone, M. J.; Maplestone, R. A.; Rahman, S. K.; Williams, D. H. Tetrahedron Lett. 1991, 32, 2663. Kotnis, A. S. Tetrahedron Lett. 1991, 32, 3441. (e) Krishnamurty, H. G.; Prasad, J. S. Tetrahedron Lett. 1975, 2511. (f) See also refs 4 and 8. (g) Shono, T.; Matsumura, Y.; Tsubata, k.; Sugihara, Y. J. Org. Chem. 1979, 44, 4508.
17. 13g see, for example: (a) Marmor, R. S. J. Org. Chem. 1972, 37, 2901. (b) Foucla, A.; Teitel, S.; Prossi, A. J. Org. Chem. 1977, 42, 3456. Stone, M. J.; Maplestone, R. A.; Rahman, S. K.; Williams, D. H. Tetrahedron Lett. 1991, 32, 2663. Kotnis, A. S. Tetrahedron Lett. 1991, 32, 3441. (e) Krishnamurty, H. G.; Prasad, J. S. Tetrahedron Lett. 1975, 2511. (f) See also refs 4 and 8. (g) Shono, T.; Matsumura, Y.; Tsubata, k.; Sugihara, Y. J. Org. Chem. 1979, 44, 4508.
18. 13g see, for example: (a) Marmor, R. S. J. Org. Chem. 1972, 37, 2901. (b) Foucla, A.; Teitel, S.; Prossi, A. J. Org. Chem. 1977, 42, 3456. Stone, M. J.; Maplestone, R. A.; Rahman, S. K.; Williams, D. H. Tetrahedron Lett. 1991, 32, 2663. Kotnis, A. S. Tetrahedron Lett. 1991, 32, 3441. (e) Krishnamurty, H. G.; Prasad, J. S. Tetrahedron Lett. 1975, 2511. (f) See also refs 4 and 8. (g) Shono, T.; Matsumura, Y.; Tsubata, k.; Sugihara, Y. J. Org. Chem. 1979, 44, 4508.
19. 13g see, for example: (a) Marmor, R. S. J. Org. Chem. 1972, 37, 2901. (b) Foucla, A.; Teitel, S.; Prossi, A. J. Org. Chem. 1977, 42, 3456. Stone, M. J.; Maplestone, R. A.; Rahman, S. K.; Williams, D. H. Tetrahedron Lett. 1991, 32, 2663. Kotnis, A. S. Tetrahedron Lett. 1991, 32, 3441. (e) Krishnamurty, H. G.; Prasad, J. S. Tetrahedron Lett. 1975, 2511. (f) See also refs 4 and 8. (g) Shono, T.; Matsumura, Y.; Tsubata, k.; Sugihara, Y. J. Org. Chem. 1979, 44, 4508.
20. 13g see, for example: (a) Marmor, R. S. J. Org. Chem. 1972, 37, 2901. (b) Foucla, A.; Teitel, S.; Prossi, A. J. Org. Chem. 1977, 42, 3456. Stone, M. J.; Maplestone, R. A.; Rahman, S. K.; Williams, D. H. Tetrahedron Lett. 1991, 32, 2663. Kotnis, A. S. Tetrahedron Lett. 1991, 32, 3441. (e) Krishnamurty, H. G.; Prasad, J. S. Tetrahedron Lett. 1975, 2511. (f) See also refs 4 and 8. (g) Shono, T.; Matsumura, Y.; Tsubata, k.; Sugihara, Y. J. Org. Chem. 1979, 44, 4508.
21. 13g see, for example: (a) Marmor, R. S. J. Org. Chem. 1972, 37, 2901. (b) Foucla, A.; Teitel, S.; Prossi, A. J. Org. Chem. 1977, 42, 3456. Stone, M. J.; Maplestone, R. A.; Rahman, S. K.; Williams, D. H. Tetrahedron Lett. 1991, 32, 2663. Kotnis, A. S. Tetrahedron Lett. 1991, 32, 3441. (e) Krishnamurty, H. G.; Prasad, J. S. Tetrahedron Lett. 1975, 2511. (f) See also refs 4 and 8. (g) Shono, T.; Matsumura, Y.; Tsubata, k.; Sugihara, Y. J. Org. Chem. 1979, 44, 4508.
22. 13g see, for example: (a) Marmor, R. S. J. Org. Chem. 1972, 37, 2901. (b) Foucla, A.; Teitel, S.; Prossi, A. J. Org. Chem. 1977, 42, 3456. Stone, M. J.; Maplestone, R. A.; Rahman, S. K.; Williams, D. H. Tetrahedron Lett. 1991, 32, 2663. Kotnis, A. S. Tetrahedron Lett. 1991, 32, 3441. (e) Krishnamurty, H. G.; Prasad, J. S. Tetrahedron Lett. 1975, 2511. (f) See also refs 4 and 8. (g) Shono, T.; Matsumura, Y.; Tsubata, k.; Sugihara, Y. J. Org. Chem. 1979, 44, 4508.
23. Corey, E. J.; Snider, B. B. J. Am. Chem. Soc. 1972, 94, 2549.
24. Some attemps to improve yields [varying reaction temperature or a different catalyst (4,4′-di-tert-butylbiphenyl)] were unsuccessful. As side products we obtained in all reactions variable amounts (<30%) of the corresponding "reduced" system (3,5-dimethoxytoluene), resulting from a proton abstraction of the benzylic organolithium intermediate from the reaction medium (see, for instance: Bates, R. B.; Kroposki, L. M.; Potter, D. E. J. Org. Chem. 1972, 37, 560 as well as ref 12b). Concerning a possible O- to C-anionic silyl migration in the starting material 3, we observed only in a few cases a small amount (<5%) of either the correponding alcohol 2 or the sililated species 12a (we thank a referee for calling our attention to this possibility).
25. Crossland, R. K.; Servis, K. L. J. Org. Chem. 1970, 35, 3195.
26. Fujimoto, Y.; Tatsuno, T. Tetrahedron Lett. 1976, 3325.
27. Blaser, H. U. Reaction at Surfaces: Opportunities and Pitfalls for the Organic Chemist. In Modern Synthetic Methods 1995; Ernst, B., Leumann, C., Eds.; VCH: Weinheim, 1995; pp 181-257.
28. Doxsee, K. M.; Feigel, M.; Stewart, K. D.; Canary, J. W.; Knobler, C. B.; Cram, D. J. J. Am. Chem. Soc. 1987, 109, 3098.
29. Gil, J. F.; Ramón, D. J.; Yus, M. Tetrahedron 1994, 50, 7307.
30. Williard, P. G.; Fryhle, C. B. Tetrahedron Lett. 1980, 21, 3731.
31. Traynelis, V. J.; Hergenrother, W. L.; Livingston, J. R.; Valicenti, J. A. J. Org. Chem. 1962, 27, 2377.
32. Wilds, A. L.; McCormack, W. B. J. Am. Chem. Soc. 1948, 70, 4127.
33. Boyle, P. H.; Davis, A. P.; Dempsey K. J.; Hosken, G. D. Tetrahedron: Asymmetry 1995, 6, 2819.
34. This behavior has been already observed in the demethylation of several compounds of type 6 or 7: see, for instance, refs 4 and 8.
35. (a) Durrani, A. A.; Tyman, J. H. P. J. Chem. Soc., Perkin Trans. 1 1980, 1658.
36. (b) Eicher, T.; Tiefensee, K.; Doing, R.; Rigobert, P. Synthesis 1991, 98.
37. Mitscher, L. A.; Park, Y. H.; Al-Shamma, A.; Hudson, P. B.; Haas, T. Phytochemistry 1981, 21, 781.
38. Almena, J.; Foubelo, F.; Yus, M. J. Org. Chem. 1994, 59, 3210.
39. Sandler, S. R.; Karo, W. Organic Functional Group Preparation; Academic Press: New York, 1971; Vol. 12-11, p 255.
40. Kim, H. J.; Jackson, W. R. Tetrahedron: Asymmetry 1994, 5, 1541.
41. Midgley, J. M.; Millership, J. S.; Whalley, W. J. Chem. Soc., Perkin Trans. 1 1976, 1384.
42. Ali, A. S.; Liepa, A. J.; Thomas, M. D.; While, J. S.; Winzenberg, K. N. Aust. J. Chem. 1994, 47, 1205. Chem. Abstr. 1994, 121, 133567d.
43. Ali, A. S.; Liepa, A. J.; Thomas, M. D.; While, J. S.; Winzenberg, K. N. Aust. J. Chem. 1994, 47, 1205. Chem. Abstr. 1994, 121, 133567d.
44. Yasuda, M.; Isami, T.; Kubo, J.; Mizutani, M.; Yamashita, T.; Shima, K. J. Org. Chem. 1992, 57, 1351.
45. Lin, C. M.; Singh, S. B.; Chu, P. S.; Dempcy, R. O.; Schmidt, J. M.; Pettit, G. R.; Hamel, E. Mol. Pharmacol. 1988, 34, 200. Chem. Abstr. 1989, 110, 68959q.
46. Lin, C. M.; Singh, S. B.; Chu, P. S.; Dempcy, R. O.; Schmidt, J. M.; Pettit, G. R.; Hamel, E. Mol. Pharmacol. 1988, 34, 200. Chem. Abstr. 1989, 110, 68959q.
47. Talvitie, A.; Marmila, E.; Kolehmainen, E. Liebigs. Ann. Chem. 1992, 399.
48. (a) Ma, G. X.; Xu, L. S.; Wang, Z. T.; Kickuchi, T. Yaoxue Xuebao 1994, 29, 763. Chem. Abstr. 1995, 112, 209764j. (b) Medarde, M.; Pelaez-Lamamie de Clairac, R.; Ramos, A. C.; Caballero, E.; Lopez, J. L.; Gravalos, D. G.; San Feliciano, A. Med. Chem. Lett. 1995, 5, 229. Chem. Abstr. 1995, 122, 239431r.
49. (a) Ma, G. X.; Xu, L. S.; Wang, Z. T.; Kickuchi, T. Yaoxue Xuebao 1994, 29, 763. Chem. Abstr. 1995, 112, 209764j. (b) Medarde, M.; Pelaez-Lamamie de Clairac, R.; Ramos, A. C.; Caballero, E.; Lopez, J. L.; Gravalos, D. G.; San Feliciano, A. Med. Chem. Lett. 1995, 5, 229. Chem. Abstr. 1995, 122, 239431r.
50. (a) Ma, G. X.; Xu, L. S.; Wang, Z. T.; Kickuchi, T. Yaoxue Xuebao 1994, 29, 763. Chem. Abstr. 1995, 112, 209764j. (b) Medarde, M.; Pelaez-Lamamie de Clairac, R.; Ramos, A. C.; Caballero, E.; Lopez, J. L.; Gravalos, D. G.; San Feliciano, A. Med. Chem. Lett. 1995, 5, 229. Chem. Abstr. 1995, 122, 239431r.
51. (a) Ma, G. X.; Xu, L. S.; Wang, Z. T.; Kickuchi, T. Yaoxue Xuebao 1994, 29, 763. Chem. Abstr. 1995, 112, 209764j. (b) Medarde, M.; Pelaez-Lamamie de Clairac, R.; Ramos, A. C.; Caballero, E.; Lopez, J. L.; Gravalos, D. G.; San Feliciano, A. Med. Chem. Lett. 1995, 5, 229. Chem. Abstr. 1995, 122, 239431r.