Metalloporphyrin-catalyzed oxidation of 2-cycloalkyl-3- hydroxynaphthoquinones

Journal of Organic Chemistry

Volumn 64, Issue 20, 1999, Pages 7330-7337

  Cunningham, Ian D ^a   Danks, Timothy N ^a   O'Connell, Keith T A ^a   Scott, Peter W ^b  

^a UNIVERSITY OF SURREY   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 NAPHTHOQUINONE DERIVATIVE; METALLOPORPHYRIN;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; OXIDATION; SYNTHESIS;

EID: 0033214273     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990297n     Document Type: Article

References (54)

1. Thomson, R. H. Naturally Occurring Quinones, 2nd ed.; Academic Press: London, 1971.
2. Arnaudon, G. Comp. Rend. 1858, 46, 1152.
3. Paterno, E. Gazz. Chim. Ital. 1882, 12, 337, 622.
4. Hooker, S. C. J. Chem. Soc. 1892, 61, 611; 1893, 63, 1376; 1896, 69, 1356.
5. Hooker, S. C. J. Chem. Soc. 1892, 61, 611; 1893, 63, 1376; 1896, 69, 1356.
6. Hooker, S. C. J. Chem. Soc. 1892, 61, 611; 1893, 63, 1376; 1896, 69, 1356.
7. Fieser, L. F.; Berliner, E.; Bondhur, F. J.; Chang, F. C.; Dauben, W. G.; Ettlinger, M. G.; Fawaz, G.; Fields, M.; Fieser, M.; Heidelberger, C.; Heymann, H.; Seligman, A. M.; Vaughan, W. R.; Wilson, A. G.; Wu, M.-I.; Leffler, M. T.; Hamlin, K. E.; Hathaway, R. J.; Matson, E. J.; Moore, E. E.; Moore, M. B.; Rapala, R. T.; Zaugg, H. E. J. Am. Chem. Soc. 1948, 70, 3151. This paper is the first and summarizing paper in a long series (parts I-XVII) covering the synthesis, antimalarial activity, and organic and physical chemistries of a wide range of 3-substituted-2-hydroxynaphtho-1,4-quinones.
8. Fieser, L. F.; Chang, F. C.; Dauben, W. G.; Heidelberger, C.; Heymann, H.; Seligman, A. M. J. Pharmacol. Exp. Ther. 1948, 94, 85.
9. McHardy, N.; Hudson, A. T.; Morgan, D. W. T.; Rae, D. G.; Dolan, T. T. Res. Vet. Sci. 1983, 35, 347. Boehm, P.; Cooper, K.; Hudson, A. T.; Elphick, J. P.; McHardy, N. J. Med. Chem. 1981, 24, 295.
10. McHardy, N.; Hudson, A. T.; Morgan, D. W. T.; Rae, D. G.; Dolan, T. T. Res. Vet. Sci. 1983, 35, 347. Boehm, P.; Cooper, K.; Hudson, A. T.; Elphick, J. P.; McHardy, N. J. Med. Chem. 1981, 24, 295.
11. (a) McHardy, N. German Patent Offenlegungsschrift 27 05 599, 10 February 1976.
12. (b) McHardy, N.; Hudson, A. T. European Patent Application 2 228, 13 June 1979; Brit. Appl. 17/48486, 22 November 1977; Chem. Abstr. 1980, 92, P163757r.
13. (b) McHardy, N.; Hudson, A. T. European Patent Application 2 228, 13 June 1979; Brit. Appl. 17/48486, 22 November 1977; Chem. Abstr. 1980, 92, P163757r.
14. (b) McHardy, N.; Hudson, A. T. European Patent Application 2 228, 13 June 1979; Brit. Appl. 17/48486, 22 November 1977; Chem. Abstr. 1980, 92, P163757r.
15. (c) Hudson, A. T.; Randall, A. W. European Patent Application 77 550, 27 April 1983; Brit. Appl. 81/31206, 16 October 1978; Chem. Abstr. 1983, 99, P87849z.
16. (c) Hudson, A. T.; Randall, A. W. European Patent Application 77 550, 27 April 1983; Brit. Appl. 81/31206, 16 October 1978; Chem. Abstr. 1983, 99, P87849z.
17. (c) Hudson, A. T.; Randall, A. W. European Patent Application 77 550, 27 April 1983; Brit. Appl. 81/31206, 16 October 1978; Chem. Abstr. 1983, 99, P87849z.
18. (d) Hudson, A. T.; Randall, A. W. European Patent Application 77 551, 27 April 1983; Brit. Appl. 81/31206, 16 October 1978, Chem. Abstr. 1983, 99, P87848y.
19. (d) Hudson, A. T.; Randall, A. W. European Patent Application 77 551, 27 April 1983; Brit. Appl. 81/31206, 16 October 1978, Chem. Abstr. 1983, 99, P87848y.
20. Hudson, A. T.; Dickens, M.; Ginger, C. D.; Gutteridge, W. E.; Holdich, T.; Huchinson, D. B.; Pudney, M.; Randall, A. W.; Latter, V. S. Drugs Exp. Clin. Res. 1991, 17, 427. Radloff, P. D.; Philipps, J.; Nkeyi, M.; Hutchinson, D.; Kremsner, P. G. Lancet 1996, 347, 1511. Torres, R. A.; Weinberg, W.; Stansell, J.; Leoung, G.; Kovacs, J.; Rogers, M.; Scott, J. Clin. Infest. Diseases 1997, 24, 422. White, A.; LaFon, S.; Rogers, M.; Andrews, E.; Brown, N. J. AIDS Human Retrovirol. 1995, 9, 280.
21. Hudson, A. T.; Dickens, M.; Ginger, C. D.; Gutteridge, W. E.; Holdich, T.; Huchinson, D. B.; Pudney, M.; Randall, A. W.; Latter, V. S. Drugs Exp. Clin. Res. 1991, 17, 427. Radloff, P. D.; Philipps, J.; Nkeyi, M.; Hutchinson, D.; Kremsner, P. G. Lancet 1996, 347, 1511. Torres, R. A.; Weinberg, W.; Stansell, J.; Leoung, G.; Kovacs, J.; Rogers, M.; Scott, J. Clin. Infest. Diseases 1997, 24, 422. White, A.; LaFon, S.; Rogers, M.; Andrews, E.; Brown, N. J. AIDS Human Retrovirol. 1995, 9, 280.
22. Hudson, A. T.; Dickens, M.; Ginger, C. D.; Gutteridge, W. E.; Holdich, T.; Huchinson, D. B.; Pudney, M.; Randall, A. W.; Latter, V. S. Drugs Exp. Clin. Res. 1991, 17, 427. Radloff, P. D.; Philipps, J.; Nkeyi, M.; Hutchinson, D.; Kremsner, P. G. Lancet 1996, 347, 1511. Torres, R. A.; Weinberg, W.; Stansell, J.; Leoung, G.; Kovacs, J.; Rogers, M.; Scott, J. Clin. Infest. Diseases 1997, 24, 422. White, A.; LaFon, S.; Rogers, M.; Andrews, E.; Brown, N. J. AIDS Human Retrovirol. 1995, 9, 280.
23. Hudson, A. T.; Dickens, M.; Ginger, C. D.; Gutteridge, W. E.; Holdich, T.; Huchinson, D. B.; Pudney, M.; Randall, A. W.; Latter, V. S. Drugs Exp. Clin. Res. 1991, 17, 427. Radloff, P. D.; Philipps, J.; Nkeyi, M.; Hutchinson, D.; Kremsner, P. G. Lancet 1996, 347, 1511. Torres, R. A.; Weinberg, W.; Stansell, J.; Leoung, G.; Kovacs, J.; Rogers, M.; Scott, J. Clin. Infest. Diseases 1997, 24, 422. White, A.; LaFon, S.; Rogers, M.; Andrews, E.; Brown, N. J. AIDS Human Retrovirol. 1995, 9, 280.
24. Fry, M, Pudney, M. Biochem. Pharmacol. 1992, 43, 1543.
25. (a) Hooker, S. C. J. Am. Chem. Soc. 1936, 58, 1168, 1174.
26. (b) Hooker, S. C.; Steyermark, A. J. Am. Chem. Soc. 1938, 58, 1179,
27. (a) Fieser, L. F.; Hartwell, J. L.; Seligman, A. M. J. Am. Chem. Soc. 1936, 58, 1223.
28. (b) Fieser, L. F.; Fieser, M. J. Am. Chem. Soc. 1948, 70, 3215.
29. Lee, K.; Turnbull, P.; Moore, H. W. J. Org. Chem. 1995, 60, 461.
30. (a) Fieser, L. F.; Bader, A. R. J. Am. Chem. Soc. 1951, 73, 681.
31. (b) Shchukina, L. A.; Shvetsov, Y. B.; Shemyakin, M. M. J. Gen. Chem. 1951, 21, 346.
32. (c) Shemyakin, M. M.; Shchukina, L. A. Quart. Rev. (London) 1956, 10, 261.
33. Fieser, L. F. J. Am. Chem. Soc. 1948, 70, 3237.
34. Meunier, B. Chem. Rev. 1992, 92, 1411. Quici, S.; Banfi, S.; Pozzi, G. Gazz. Chim. Ital. 1993, 123, 597. Hirobe, M. Pure. Appl. Chem. 1994, 66, 729. Shingaki, T.; Miura, K.; Higuchi, T.; Hirobe, M.; Nagano, T. Chem. Commun. 1997, 861. Nakano, T.; Agatsuma, N.; Kodama, S.; Kakuda, H.; Dolphin, D. Bull. Chim. Soc. Jpn. 1996, 69, 3513. El-Kasami, D.; Tetreau, C.; Lavalette, D.; Momenteau, M. J. Am. Chem. Soc. 1995, 117, 6041.
35. Meunier, B. Chem. Rev. 1992, 92, 1411. Quici, S.; Banfi, S.; Pozzi, G. Gazz. Chim. Ital. 1993, 123, 597. Hirobe, M. Pure. Appl. Chem. 1994, 66, 729. Shingaki, T.; Miura, K.; Higuchi, T.; Hirobe, M.; Nagano, T. Chem. Commun. 1997, 861. Nakano, T.; Agatsuma, N.; Kodama, S.; Kakuda, H.; Dolphin, D. Bull. Chim. Soc. Jpn. 1996, 69, 3513. El-Kasami, D.; Tetreau, C.; Lavalette, D.; Momenteau, M. J. Am. Chem. Soc. 1995, 117, 6041.
36. Meunier, B. Chem. Rev. 1992, 92, 1411. Quici, S.; Banfi, S.; Pozzi, G. Gazz. Chim. Ital. 1993, 123, 597. Hirobe, M. Pure. Appl. Chem. 1994, 66, 729. Shingaki, T.; Miura, K.; Higuchi, T.; Hirobe, M.; Nagano, T. Chem. Commun. 1997, 861. Nakano, T.; Agatsuma, N.; Kodama, S.; Kakuda, H.; Dolphin, D. Bull. Chim. Soc. Jpn. 1996, 69, 3513. El-Kasami, D.; Tetreau, C.; Lavalette, D.; Momenteau, M. J. Am. Chem. Soc. 1995, 117, 6041.
37. Meunier, B. Chem. Rev. 1992, 92, 1411. Quici, S.; Banfi, S.; Pozzi, G. Gazz. Chim. Ital. 1993, 123, 597. Hirobe, M. Pure. Appl. Chem. 1994, 66, 729. Shingaki, T.; Miura, K.; Higuchi, T.; Hirobe, M.; Nagano, T. Chem. Commun. 1997, 861. Nakano, T.; Agatsuma, N.; Kodama, S.; Kakuda, H.; Dolphin, D. Bull. Chim. Soc. Jpn. 1996, 69, 3513. El-Kasami, D.; Tetreau, C.; Lavalette, D.; Momenteau, M. J. Am. Chem. Soc. 1995, 117, 6041.
38. Meunier, B. Chem. Rev. 1992, 92, 1411. Quici, S.; Banfi, S.; Pozzi, G. Gazz. Chim. Ital. 1993, 123, 597. Hirobe, M. Pure. Appl. Chem. 1994, 66, 729. Shingaki, T.; Miura, K.; Higuchi, T.; Hirobe, M.; Nagano, T. Chem. Commun. 1997, 861. Nakano, T.; Agatsuma, N.; Kodama, S.; Kakuda, H.; Dolphin, D. Bull. Chim. Soc. Jpn. 1996, 69, 3513. El-Kasami, D.; Tetreau, C.; Lavalette, D.; Momenteau, M. J. Am. Chem. Soc. 1995, 117, 6041.
39. Meunier, B. Chem. Rev. 1992, 92, 1411. Quici, S.; Banfi, S.; Pozzi, G. Gazz. Chim. Ital. 1993, 123, 597. Hirobe, M. Pure. Appl. Chem. 1994, 66, 729. Shingaki, T.; Miura, K.; Higuchi, T.; Hirobe, M.; Nagano, T. Chem. Commun. 1997, 861. Nakano, T.; Agatsuma, N.; Kodama, S.; Kakuda, H.; Dolphin, D. Bull. Chim. Soc. Jpn. 1996, 69, 3513. El-Kasami, D.; Tetreau, C.; Lavalette, D.; Momenteau, M. J. Am. Chem. Soc. 1995, 117, 6041.
40. Ettlinger, M. G. J. Am. Chem. Soc. 1960, 72, 3472.
41. -1 peak.
42. Fieser, L. F. J. Am. Chem. Soc. 1941, 63, 2948.
43. a value for 1a of 3.98 at 25 °C) rising to >6 in more organic solvents (e.g., 50% acetone:water). See: Fieser, L. F.; Fieser, M. J. Am. Chem. Soc. 1934, 56, 1565. Ball, E. G. J. Biol. Chem. 1934, 106, 515.
44. a value for 1a of 3.98 at 25 °C) rising to >6 in more organic solvents (e.g., 50% acetone:water). See: Fieser, L. F.; Fieser, M. J. Am. Chem. Soc. 1934, 56, 1565. Ball, E. G. J. Biol. Chem. 1934, 106, 515.
45. -) to the less electron-rich (-OMe) C=C.; third, the bulk of the 2-cycloalkyl substituents would favor the "electrophilic approach" from above the C=C.
46. -) to the less electron-rich (-OMe) C=C.; third, the bulk of the 2-cycloalkyl substituents would favor the "electrophilic approach" from above the C=C.
47. -) to the less electron-rich (-OMe) C=C.; third, the bulk of the 2-cycloalkyl substituents would favor the "electrophilic approach" from above the C=C.
48. -) to the less electron-rich (-OMe) C=C.; third, the bulk of the 2-cycloalkyl substituents would favor the "electrophilic approach" from above the C=C.
49. -) to the less electron-rich (-OMe) C=C.; third, the bulk of the 2-cycloalkyl substituents would favor the "electrophilic approach" from above the C=C.
50. March, J. Advanced Organic Chemistry, 4th ed.; Wiley-Interscience: New York, 1991; p 369.
51. Ortiz de Montellano, P. R. Cytochrome P450, Structure, Mechanism and Biochemistry, 2nd ed.; Plenum: New York, 1995; p 264.
52. Fieser, L. F. J. Am. Chem. Soc. 1948, 70, 3165.
53. Lindner, W.; Becker, B.; Steffans, R.; Wachendorf-Neumann, U.; Brandes, W.; Dutzmann, S.; Stendel, W. German Patent Offenlegungsschrift 3801 743, 19 January 1989; Chem. Abstr. 1989, 111, P7086b.
54. Lindner, W.; Becker, B.; Steffans, R.; Wachendorf-Neumann, U.; Brandes, W.; Dutzmann, S.; Stendel, W. German Patent Offenlegungsschrift 3801 743, 19 January 1989; Chem. Abstr. 1989, 111, P7086b.