Synthesis of 2H-1-benzopyrans by Pd-catalyzed cyclization of o-allylic phenols

Synlett

Volumn , Issue 5, 1998, Pages 522-524

  Larock, Richard C ^a   Wei, Lulin ^a   Hightower, Timothy R ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 26844528632     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1709     Document Type: Article

References (54)

1. (a) Dean, F. M. "The Total Synthesis of Naturally Occurring Oxygen Ring Compounds," ApSimon, J., Ed.; Wiley Interscience: New York, 1973; Vol. 1, p 467.
2. (b) Ellis, G. P. "Chromenes, Chromanones, and Chromones," John Wiley and Sons: New York, 1977.
3. (c) Passreiter, C. M.; Willuhn, G.; Steigel, A.; Matthiesen, U. Phytochemistry 1992, 31, 1070;
4. (d) Merlini, L. Adv. Heterocyl. Chem. 1975, 18, 159.
5. (a) Narkhede, D. D.; Iyer, P. R.; Iyer, C. S. R. Tetrahedron 1990, 46, 2031.
6. (b) Engler, T. A.; Lynch, K. O., Jr.; Reddy, J. P.; Gregory, G. S. Bioorg. Med. Chem. Lett. 1993, 3, 1229.
7. (a) Billeret, D.; Blondeau, D.; Sliwa, H. Synthesis 1993, 881, and references cited therein.
8. (b) Barton, D. H. R.; Donnelly, D. M. X.; Finet, J.; Guiry, P. J. Tetrahedron Lett. 1990, 31, 7449.
9. Garcías, X.; Ballester, P.; Saá, J. M. Tetrahedron Lett. 1991, 32, 7739.
10. (a) Bongini, A.; Cardillo, G.; Orena, M.; Porzi, G.; Sandri, S. Tetrahedron Lett. 1979, 2545.
11. (b) Jurd, L.; Manners, G. D. Synthesis 1980, 618.
12. Clive, D. L. J.; Chittattu, G.; Curtis, N. J.; Kiel, W. A.; Wong, C. K. J. Chem. Soc., Chem. Commun. 1977, 725.
13. (a) Cardillo, G.; Cricchio, R.; Merlini, L. Tetrahedron 1968, 24, 4825.
14. (b) Mechoulam, R.; Yagnitinsky, B.; Gaoni, Y. J. Am. Chem. Soc. 1968, 90, 2418.
15. (c) Cardillo, G.; Cricchio, R.; Merlini, L.; Nasini, G. Gazz. Chim. Ital. 1969, 99, 308.
16. (d) Nozoe, S.; Suzuki, K.T. Tetrahedron Lett. 1969, 29, 2457.
17. (e) Jain, A. C.; Lal, P.; Seshadri, T. R. Tetrahedron 1970, 26, 1977.
18. (f) Hlubucek, J.; Ritchie, E.; Taylor, W. C. Aust. J. Chem. 1970, 23, 1881.
19. (g) Jain, A. C.; Khanna, V. K.; Lal, P.; Seshadri, T. R. Ind. J. Chem. 1970, 8, 480.
20. (h) Bajwa, B. S.; Khanna, P. L.; Seshadri, T. R. Ind. J. Chem. 1971, 9, 1322.
21. (i) Bala, K. R.; Seshadri, T. R. Phytochemistry 1971, 10, 1131.
22. (j) Steck, W. Can. J. Chem. 1971, 49, 2297.
23. (k) Carpenter, I.; McGarry, E. J.; Scheinmann, F. J. Chem. Soc. C 1971, 3783.
24. (l) Jain, A. C.; Jain, S. M. Tetrahedron Lett. 1972, 28, 759.
25. (m) Deshpande, V.H.; Rama Rao, A. V.; Srinivasan, R.; Venkataraman K. Ind. J. Chem 1972, 10, 681.
26. (n) Jain, A. C.; Jain, S. M. Tetrahedron 1972, 28, 981.
27. (o) Anand, S. M.; Jain, A. C. Tetrahedron 1972, 28, 987.
28. (p) Jain, A. C.; Jain, S. M. Tetrahedron 1972, 28, 5063.
29. (q) Meikle, T.; Stevens, R. Tetrahedron Lett. 1972, 4787.
30. (r) Jain, A. C.; Zutshi, M. K. Aust. J. Chem. 1973, 26, 641.
31. (s) Monache, F. D.; De Lima, O. G.; De Mello, J. F.; Monache, G. D.; Marini-Bettòlo, G. B. Gazz. Chim. Ital. 1973, 103, 779.
32. (t) Jain, A. C.; Jain, S. M. Tetrahedron 1973, 29, 2803.
33. (u) Cardillo, G.; Orena, M.; Porzi, G.; Sandri, S. J. Chem. Soc., Chem. Commun. 1979, 836.
34. (a) Hosokawa, T.; Ohkata, H.; Moritani, I. Bull. Chem. Soc. Jpn. 1975, 48, 1533.
35. (b) Hosokawa, T.; Maeda, K.; Koga, K.; Moritani, I. Tetrahedron Lett. 1973, 739.
36. Hosokawa, T.; Yamashita, S.; Murahashi, S.; Sonoda, A. Bull. Chem. Soc. Jpn. 1976, 49, 3662.
37. Hosokawa, T.; Miyagi, S.; Murahashi, S.; Sonada, A. J. Org. Chem. 1978, 43, 2752.
38. (a) Hosakawa, T.; Uno, T.; Inui, S.; Murahashi, S.-I. J. Am. Chem. Soc. 1981, 103, 2318.
39. (b) Hosokawa, T.; Imada, Y.; Murahashi, S.-I. Bull. Chem. Soc. Jpn. 1985, 58, 3282.
40. (c) Hosokawa, T.; Okuda, C.; Murahashi, S.-I. J. Org. Chem. 1985, 50, 1282.
41. Uozumi, Y.; Kato, K.; Hayashi, T. J. Am. Chem. Soc. 1997, 119, 5063.
42. (a) Larock, R. C.; Hightower, T. R. J. Org. Chem. 1993, 58, 5298.
43. (b) Larock, R. C.; Hightower, T. R.; Kraus, G. A.; Hahn, P.; Zheng, D. Tetrahedron Lett. 1995, 36, 2423.
44. (c) Larock, R. C.; Hightower, T. R.; Hasvold, L. A.; Peterson, K. P. J. Org. Chem. 1996, 61, 3584.
45. (a) van Benthem, R. A. T. M.; Hiemstra, H.; Michels, J. J.; Speckamp, W. N. J. Chem. Soc., Chem. Commun. 1994, 357.
46. (b) van Benthem, R. A. T. M.; Hiemstra, H.; Longarela, G. R.; Speckamp, W. N. Tetrahedron Lett. 1994, 35, 9281.
47. (c) Rönn, M.; Bäckvall, J.; Andersson, P. G. Tetrahedron Lett. 1995, 36, 7749.
48. (a) Tiabi, M.; Zamarlik, H. Tetrahedron Lett. 1991, 32, 7251.
49. (b) Timár, T.; Jászberényi, J. C. J. Heterocycl. Chem. 1988, 25, 871.
50. North, J. T.; Kronenthal, D. R.; Pullockaran, A. J.; Real, S. D.; Chen, H. Y. J. Org. Chem. 1995, 60, 3397.
51. (a) Tsuji, J. "Organic Synthesis with Palladium Compounds"; Springer: Berlin, Heidelberg, New York; 1980.
52. (b) Heck, R. F. "Palladium Reagents in Organic Synthesis"; Academic Press: New York, 1985.
53. (c) Tsuji, J. "Palladium Reagents and Catalysts: Innovations in Organic Synthesis", John Wiley & Sons: Chichester, New York, Brisbane, Toronto, Singapore; 1995.
54. (d) van der Schaaf, P. A.; Sutler, J.-P.; Grellier, M.; van Mier, G. P. M.; Spek, A. L.; van Koten, G.; Pfeffer, M. J. Am. Chem. Soc. 1994, 116, 5134.