Polycyclic Aromatic Compounds via Radical Cyclizations of Benzannulated Enyne-Allenes Derived from Ireland-Claisen Rearrangement

Journal of Organic Chemistry

Volumn 68, Issue 22, 2003, Pages 8545-8549

  Yang, Yonghong ^a   Petersen, Jeffrey L ^a   Wang, Kung K ^a  

^a WEST VIRGINIA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

RADICAL CYCLIZATIONS;

ACYLATION; ADDITION REACTIONS; FREE RADICALS; HYDROLYSIS;

POLYCYCLIC AROMATIC HYDROCARBONS;

1H CYCLOBUT[A]INDENYL ACETIC ACID; 9 FLUORENONE; ACETAL DERIVATIVE; ALLENE DERIVATIVE; CARBOXYLIC ACID; FLUORINE DERIVATIVE; POLYCYCLIC AROMATIC COMPOUND; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CLAISEN REARRANGEMENT; CYCLIZATION; DIELS ALDER REACTION; HYDROLYSIS; SYNTHESIS;

EID: 0142227963     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035036z     Document Type: Article

References (59)

1. For reviews, see: (a) Nicolaou, K. C.; Dai, W.-H. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387-1416.
2. (b) Maier, M. E. Synlett 1995, 13-26.
3. (c) Wang, K. K. Chem. Rev. 1996, 96, 207-222.
4. (d) Saito, I.; Nakatani, K. Bull. Chem. Soc. Jpn. 1996, 69, 3007-3019.
5. (e) Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453-6518.
6. (a) Myers, A. G.; Kuo, E. Y.; Finney, N. S. J. Am. Chem. Soc. 1989, 111, 8057-8059.
7. (b) Myers, A. G.; Dragovich, P. S. J. Am. Chem. Soc. 1989, 111, 9130-9132.
8. (c) Nagata, R.; Yamanaka, H.; Okazaki, E.; Saito, I. Tetrahedron Lett. 1989, 30, 4995-4998.
9. (d) Nagata, R.; Yamanaka, H.; Murahashi, E.; Saito, I. Tetrahedron Lett. 1990, 31, 2907-2910.
10. (a) Schmittel, M.; Strittmatter, M.; Kiau, S. Tetrahedron Lett. 1995, 36, 4975-4978.
11. (b) Schmittel, M.; Strittmatter, M.; Vollmann, K.; Kiau, S. Tetrahedron Lett. 1996, 37, 999-1002.
12. (c) Schmittel, M.; Strittmatter, M.; Kiau, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 1843-1845.
13. (d) Schmittel, M.; Kiau, S.; Siebert, T.; Strittmatter, M. Tetrahedron Lett. 1996, 37, 7691-7694.
14. (e) Schmittel, M.; Keller, M.; Kiau, S.; Strittmatter, M. Chem.-Eur. J. 1997, 3, 807-816.
15. (f) Schmittel, M.; Steffen, J.-P.; Maywald, M.; Engels, B.; Helten, H.; Musch, P. J. Chem. Soc., Perkin Trans. 2 2001, 1331-1339.
16. (a) Grissom, J. W.; Klingberg, D.; Huang, D.; Slattery, B. J. J. Org. Chem. 1997, 62, 603-606.
17. (b) Grissom, J. W.; Huang, D. J. Org. Chem. 1994, 59, 5114-5116.
18. Baldwin, J. E.; Bennett, P. A. R.; Forrest, A. K. J. Chem. Soc., Chem. Commun. 1987, 250-251.
19. Li, H.; Petersen, J. L.; Wang, K. K. J. Org. Chem. 2001, 66, 7804-7810.
20. Li, H.; Zhang, H.-R.; Petersen, J. L.; Wang, K. K. J. Org. Chem. 2001, 66, 6662-6668.
21. (a) Ireland, R. E.; Mueller, R. H.; Willard, A. K. J. Am. Chem. Soc. 1976, 98, 2868-2877.
22. (b) Rathke, M. W.; Sullivan, D. F. Synth. Commun. 1973, 3, 67-72.
23. (a) Harvey, R. G.; Abu-shqara, E.; Yang, C. J. Org. Chem. 1992, 57, 6313-6317.
24. (b) Muzart, J. Tetrahedron Lett. 1987, 28, 2131-2132.
25. (a) Yang, C. X.; Harvey, R. G. Polycyclic Aromat. Compd. 1992, 2, 229-233.
26. (b) Harvey, R. G. Polycyclic Aromatic Hydrocarbons; Wiley: New York, 1997; pp 336-337.
27. The structure was established by X-ray structure analysis (see Supporting Information).
28. (a) Yoshida, M.; Kadokura, A.; Minabe, M. Bull. Chem. Soc. Jpn. 1980, 53, 1179-1180.
29. (b) Barth, W. E.; Lawton, R. G. J. Am. Chem. Soc. 1971, 93, 1730-1745.
30. (c) Barth, W. E.; Lawton, R. G. J. Am. Chem. Soc. 1966, 88, 380-381.
31. (a) Chang, H.-F.; Cho, B. P. J. Org. Chem. 1999, 64, 9051-9056.
32. (b) Crombie, D. A.; Shaw, S. J. Chem. Soc. C 1969, 2489-2490.
33. (c) Dosa, P. I.; Schleifenbaum, A.; Vollhardt, K. P. C. Org. Lett. 2001, 3, 1017-1020.
34. (d) Brooks, M. A.; Scott, L. T. J. Am. Chem. Soc. 1999, 121, 5444-5449.
35. (e) Sarobe, M.; Jenneskens, L. W.; Wiersum, U. E. Tetrahedron Lett. 1997, 38, 4689-4692.
36. (f) Plater, M. J. Tetrahedron Lett. 1994, 35, 6147-6150.
37. (g) Studt, P.; Win, T. Liebigs Ann. Chem. 1983, 519.
38. (a) Scott, L. T.; Cheng, P.-C.; Hashemi, M. M.; Bratcher, M. S.; Meyer, D. T.; Warren, H. B. J. Am. Chem. Soc. 1997, 119, 10963-10968.
39. (b) Reisch, H. A.; Bratcher, M. S.; Scott, L. T. Org. Lett. 2000, 2, 1427-1430.
40. (c) Ansems, R. B. M.; Scott, L. T. J. Am. Chem. Soc. 2000, 122, 2719-2724.
41. (d) Bronstein, H. E.; Choi, N.; Scott, L. T. J. Am. Chem. Soc. 2002, 124, 8870-8875.
42. (e) Sygula, A.; Rabideau, P. W. J. Am. Chem. Soc. 1998, 120, 12666-12667.
43. (f) Sygula, A.; Rabideau, P. W. J. Am. Chem. Soc. 1999, 121, 7800-7803.
44. (g) Sygula, A.; Rabideau, P. W. J. Am. Chem. Soc. 2000, 122, 6323-6324.
45. (h) Sygula, A.; Xu, G.; Marcinow, Z.; Rabideau, P. W. Tetrahedron 2001, 57, 3637-3644.
46. (i) Marcinow, Z.; Grove, D. I.; Rabideau, P. W. J. Org. Chem. 2002, 67, 3537-3539.
47. (j) Sygula, A.; Karlen, S. D.; Sygula, R.; Rabideau, P. W. Org. Lett. 2002, 4, 3135-3137.
48. (k) Seiders, T. J.; Baldridge, K. K.; Siegel, J. S. J. Am. Chem. Soc. 1996, 118, 2754-2755.
49. (l) Mehta, G.; Sarma, P. V. V. S. Chem. Commun. 2000, 19-20.
50. For reviews, see: (m) Scott, L. T.; Bronstein, H. E.; Preda, D. V.; Ansems, R. B. M.; Bratcher, M. S.; Hagen, S. Pure Appl. Chem. 1999, 71, 209-219.
51. (n) Mehta, G.; Rao, H. S. P. Tetrahedron 1998, 54, 13325-13370.
52. (o) Rabideau, P. W.; Sygula, A. Acc. Chem. Res. 1996, 29, 235-242.
53. (p) Scott, L. T. Pure Appl. Chem. 1996, 68, 291-300.
54. (a) Nongrum, F. M.; Myrboh, B. Synthesis 1987, 845-846.
55. (b) Taylor, E. C.; Chiang, C.-S.; McKillop, A.; White, J. F. J. Am. Chem. Soc. 1976, 98, 6750-6752.
56. (c) Wiberg, K. B.; Furtek, B. L.; Olli, L. K. J. Am. Chem. Soc. 1979, 101, 7675-7679.
57. (a) Klemm, L. H.; Shabtai, J.; Taylor, D. R. J. Org. Chem. 1968, 33, 1480-1488.
58. (b) Zimmerman, H. E.; Factor, R. E. J. Am. Chem. Soc. 1980, 102, 3538-3548.
59. Lemmen, P.; Lenoir, D. Chem. Ber. 1984, 117, 2300-2313.