A convergent approach to coenzyme Q

Journal of the American Chemical Society

Volumn 121, Issue 50, 1999, Pages 11664-11673

  Lipshutz, Bruce H ^a   Bulow, Gerd ^a   Fernandez Lazaro, Fernando ^a   Kim, Sung Kyu ^a   Lowe, Richard ^a   Mollard, Paul ^a   Stevens, Kirk L ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HALIDE; PLASTOQUINONE; QUINONE DERIVATIVE; UBIQUINONE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CONTROLLED STUDY; ENZYME STRUCTURE; ENZYME SYNTHESIS;

EID: 0033596318     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja992164p     Document Type: Article

References (69)

1. (a) Thomson, R. H. In Naturally Occurring Quinones; Academic Press: N.Y., 1971.
2. (b) Combs, A. B.; Acosta, D.; Folkers, K. IRCS Med. Sci.: Libr. Compend. 1976, 4, 403.
3. (c) Heller, J. H.; Perspect. Biol. Med. 1973, 16, 181.
4. (d) Littaru, G. P.; Ho, L.; Folkers, K. Int. J. Vitam. Nutr. Res. 1972, 42, 291, 413.
5. (e) Biomedical and Clinical Aspects of Coenzyme Q; Folkers, K., Yamamura, Y., Eds.; Elsevier: Amsterdam, Vol. 1-4.
6. (f) Coenzyme Q; Lenaz, G., Ed., Wiley: New York, 1985.
7. (g) Trumpower, B. L. Function of Ubiquinones in Energy Conserving Systems; Academic Press: New York, 1982.
8. (h) Thomson, R. H. Naturally Occurring Quinones, 3rd ed.; Academic Press: New York, 1987.
9. 10; Bantom Books: New York, 1987.
10. Sasikala, Ch.; Ramana, Ch. V. Adv. Appl. Microbiol. 1995, 41, 173.
11. Sigma-Aldrich Catalog; Sigma-Aldrich: St. Louis, 1998; pp 306-307.
12. For representative alternative approaches to controlling olefin geometry in polyprenoidal systems, see Mechelke, M. F.; Wiemer, D. F. Tetrahedron Lett. 1998, 39, 783. Saa, J. M.; Ballester, P.; Deya, P. M.; Capo, M.; Garcias, X. J. Org. Chem. 1996, 61, 1035. Garcias, X.; Ballester, P.; Capo, M.; Saa, J. M. ibid. 1994, 59, 5093;
13. For representative alternative approaches to controlling olefin geometry in polyprenoidal systems, see Mechelke, M. F.; Wiemer, D. F. Tetrahedron Lett. 1998, 39, 783. Saa, J. M.; Ballester, P.; Deya, P. M.; Capo, M.; Garcias, X. J. Org. Chem. 1996, 61, 1035. Garcias, X.; Ballester, P.; Capo, M.; Saa, J. M. ibid. 1994, 59, 5093;
14. For representative alternative approaches to controlling olefin geometry in polyprenoidal systems, see Mechelke, M. F.; Wiemer, D. F. Tetrahedron Lett. 1998, 39, 783. Saa, J. M.; Ballester, P.; Deya, P. M.; Capo, M.; Garcias, X. J. Org. Chem. 1996, 61, 1035. Garcias, X.; Ballester, P.; Capo, M.; Saa, J. M. ibid. 1994, 59, 5093;
15. Duralski, A. A.; Watts, A. Tetrahedron Lett. 1992, 34, 4983. Yanagisawa, A.; Nomura, N.; Noritake, Y.; Yamamoto, H. Synthesis 1991, 1130. Eto, H.; Eguchi, C. Chem. Lett. 1988, 1597. Naruta, Y. J. Org. Chem. 1980, 45, 4097. Inoue, S.; Yamaguchi, R.; Saito, K.; Sato, K. Bull. Chem. Soc. Jpn. 1974, 47, 3098.
16. Duralski, A. A.; Watts, A. Tetrahedron Lett. 1992, 34, 4983. Yanagisawa, A.; Nomura, N.; Noritake, Y.; Yamamoto, H. Synthesis 1991, 1130. Eto, H.; Eguchi, C. Chem. Lett. 1988, 1597. Naruta, Y. J. Org. Chem. 1980, 45, 4097. Inoue, S.; Yamaguchi, R.; Saito, K.; Sato, K. Bull. Chem. Soc. Jpn. 1974, 47, 3098.
17. Duralski, A. A.; Watts, A. Tetrahedron Lett. 1992, 34, 4983. Yanagisawa, A.; Nomura, N.; Noritake, Y.; Yamamoto, H. Synthesis 1991, 1130. Eto, H.; Eguchi, C. Chem. Lett. 1988, 1597. Naruta, Y. J. Org. Chem. 1980, 45, 4097. Inoue, S.; Yamaguchi, R.; Saito, K.; Sato, K. Bull. Chem. Soc. Jpn. 1974, 47, 3098.
18. Duralski, A. A.; Watts, A. Tetrahedron Lett. 1992, 34, 4983. Yanagisawa, A.; Nomura, N.; Noritake, Y.; Yamamoto, H. Synthesis 1991, 1130. Eto, H.; Eguchi, C. Chem. Lett. 1988, 1597. Naruta, Y. J. Org. Chem. 1980, 45, 4097. Inoue, S.; Yamaguchi, R.; Saito, K.; Sato, K. Bull. Chem. Soc. Jpn. 1974, 47, 3098.
19. Duralski, A. A.; Watts, A. Tetrahedron Lett. 1992, 34, 4983. Yanagisawa, A.; Nomura, N.; Noritake, Y.; Yamamoto, H. Synthesis 1991, 1130. Eto, H.; Eguchi, C. Chem. Lett. 1988, 1597. Naruta, Y. J. Org. Chem. 1980, 45, 4097. Inoue, S.; Yamaguchi, R.; Saito, K.; Sato, K. Bull. Chem. Soc. Jpn. 1974, 47, 3098.
20. (a) Eren, D.; Keinan, E. J. Am. Chem. Soc. 1988, 110, 4356.
21. (b) Mohri, M.; Kinoshita, H.; Inomata, K.; Kotake, H.; Takagaki, H.; Yamazaki, K. Chem. Lett. 1986, 1177.
22. (c) Araki, S.; Sato, T.; Miyagawa, H.; Butsugan, Y. Bull. Chem. Soc. Jpn. 1984, 57, 3523.
23. (d) Terao, S.; Kato, K.; Shiraishi, M.; Morimoto, H. J. Chem. Soc., Perkin Trans. 1 1978, 1101.
24. (e) Terao, S.; Kato, K.; Shiraishi, M.; Morimoto, H. J. Org. Chem. 1979, 44, 868.
25. Rüttimann, A.; Lorenz, P. Helv. Chim. Acta 1990, 73, 790. Van Lient, W. B. S.; Steggerda, W. F.; Esmeijer, R.; Lugtenburg, J. Recl. Trav. Chim. Pays-Bas 1994, 113, 153.
26. Rüttimann, A.; Lorenz, P. Helv. Chim. Acta 1990, 73, 790. Van Lient, W. B. S.; Steggerda, W. F.; Esmeijer, R.; Lugtenburg, J. Recl. Trav. Chim. Pays-Bas 1994, 113, 153.
27. Hegedus, L. S. Transition Metals in the Synthesis of Complex Organic Molecules; University Science Books: Mill Valley, CA, 1994.
28. Obtained from Kuraray Co., Ltd., Kurashiki City, Japan.
29. Van Horn, D. E.; Negishi, E. J. Am. Chem. Soc. 1978, 100, 2252. Negishi, E.; Van Horn, D. E.; Yoshida, T. J. Am. Chem. Soc. 1985, 107, 6639. Matsushita, H.; Negishi, E. Org. Synth. 1984, 63, 31. Negishi, E. Pure Appl. Chem. 1981, 53, 2333.
30. Van Horn, D. E.; Negishi, E. J. Am. Chem. Soc. 1978, 100, 2252. Negishi, E.; Van Horn, D. E.; Yoshida, T. J. Am. Chem. Soc. 1985, 107, 6639. Matsushita, H.; Negishi, E. Org. Synth. 1984, 63, 31. Negishi, E. Pure Appl. Chem. 1981, 53, 2333.
31. Van Horn, D. E.; Negishi, E. J. Am. Chem. Soc. 1978, 100, 2252. Negishi, E.; Van Horn, D. E.; Yoshida, T. J. Am. Chem. Soc. 1985, 107, 6639. Matsushita, H.; Negishi, E. Org. Synth. 1984, 63, 31. Negishi, E. Pure Appl. Chem. 1981, 53, 2333.
32. Van Horn, D. E.; Negishi, E. J. Am. Chem. Soc. 1978, 100, 2252. Negishi, E.; Van Horn, D. E.; Yoshida, T. J. Am. Chem. Soc. 1985, 107, 6639. Matsushita, H.; Negishi, E. Org. Synth. 1984, 63, 31. Negishi, E. Pure Appl. Chem. 1981, 53, 2333.
33. Negishi, E. I.; Matsushita, H.; Okukado, N. Tetrahedron Lett. 1981, 22, 2715.
34. (a) Yanagisawa, A.; Habaue, S.; Yamamoto, H. J. Am. Chem. Soc. 1991, 113, 8955; ibid. 1991, 113, 5893. Corey, E. J.; Shieh, W.-C. Tetrahedron Lett. 1992, 33, 6435.
35. (a) Yanagisawa, A.; Habaue, S.; Yamamoto, H. J. Am. Chem. Soc. 1991, 113, 8955; ibid. 1991, 113, 5893. Corey, E. J.; Shieh, W.-C. Tetrahedron Lett. 1992, 33, 6435.
36. (a) Yanagisawa, A.; Habaue, S.; Yamamoto, H. J. Am. Chem. Soc. 1991, 113, 8955; ibid. 1991, 113, 5893. Corey, E. J.; Shieh, W.-C. Tetrahedron Lett. 1992, 33, 6435.
37. (b) Sato, K.; Inoue, S.; Onishi, A.; Uchida, N.; Minowa, N. J. Chem. Soc., Perkin Trans. 1 1981, 761.
38. Masaki, Y.; Hasimoto, K.; Sakuma, K.; Kaji, K. Chem. Pharm. Bull. 1984, 32, 3952.
39. Altman, I. J.; Ash, L.; Marson, S. Synthesis 1974, 129.
40. Keinan, E.; Eren, D. J. Org. Chem. 1987, 52, 3872.
41. Shunk, C. H.; Wolf, D. E.; McPherson, J. F.; Linn, B. O.; Folkers, K. J. Am. Chem. Soc. 1960, 82, 5914.
42. (a) Corey, E. J.; Rucker, C. Tetrahedron Lett. 1982, 23, 719.
43. (b) Lipshutz, B. H.; Koerner, M.; Parker, D. A. ibid. 1987, 28, 945. Lipshutz, B. H. In Organometallics in Synthesis: A Manual; Schlosser, M., Ed., Wiley: 1994; pp 283-382.
44. (b) Lipshutz, B. H.; Koerner, M.; Parker, D. A. ibid. 1987, 28, 945. Lipshutz, B. H. In Organometallics in Synthesis: A Manual; Schlosser, M., Ed., Wiley: 1994; pp 283-382.
45. Cahiez, G.; Alexakis, A.; Normant, J. Synthesis 1978, 528.
46. Negishi, E.; Takahashi, T.; Akiyoshi, K. J. Chem. Soc., Chem. Commun. 1986, 1338.
47. Lipshutz, B. H.; Bulow, G.; Lowe, R.; Stevens, K. L. J. Am. Chem. Soc. 1996, 118, 5512.
48. Taniguchi, T.; Ogasawara, K. Angew. Chem., Int. Ed. 1998, 37, 1136; Tetrahedron Lett. 1998, 39, 4679.
49. Taniguchi, T.; Ogasawara, K. Angew. Chem., Int. Ed. 1998, 37, 1136; Tetrahedron Lett. 1998, 39, 4679.
50. Corey, E. J.; Kim, C. U.; Takeda, M. Tetrahedron Lett. 1972, 4339.
51. Mohri, M.; Kinoshita, H.; Inomata, K.; Kotake, H. Chem. Lett. 1985, 451 and references therein.
52. The corresponding bromomethylated p-benzoquinone has been prepared en route to vitamin K; cf. Rüttimann, A. Chimia 1986, 40, 290.
53. Ascenso, J. R.; de C. T. Carrondo, M. A. A. F.; Dias, A. R.; Gomes, P. T.; Piedade, M. F. M.; Romao, C. C.; Revillon, A.; Tkatchenko, I. Polyhedron 1989, 8, 2449.
54. Grushin, V. V.; Alper, H. Chem. Rev. 1994, 94, 1047. Morrell, D. G.; Kochi, J. K. J. Am. Chem. Soc. 1975, 97, 7262. Tsou, T. T.; Kochi, J. K. ibid. 1979, 101, 6319.
55. Grushin, V. V.; Alper, H. Chem. Rev. 1994, 94, 1047. Morrell, D. G.; Kochi, J. K. J. Am. Chem. Soc. 1975, 97, 7262. Tsou, T. T.; Kochi, J. K. ibid. 1979, 101, 6319.
56. Grushin, V. V.; Alper, H. Chem. Rev. 1994, 94, 1047. Morrell, D. G.; Kochi, J. K. J. Am. Chem. Soc. 1975, 97, 7262. Tsou, T. T.; Kochi, J. K. ibid. 1979, 101, 6319.
57. Lipshutz, B. H.; Kim, S.-K.; Stevens, K. L.; Mollard, P. Tetrahedron 1998, 54, 1241.
58. Miyakado, M.; Ohno, N.; Yoshioka, H.; Mabry, T. Phytochemistry 1978, 17, 143.
59. Schmid, M.; Gerber, F.; Hirth, G. Helv. Chim. Acta 1982, 65, 684.
60. Tsuji, J. Palladium Reagents and Catalysis; John Wiley and Sons Ltd.: Chichester, 1995.
61. New Developments in Organonickel Chemistry, Lipshutz, B. H., Luh, T.-Y., Eds.; Tetrahedron Symposium-in-Print 1998, 54, 1021-1316.
62. Eis, K.; Schmalz, H.-G. Synthesis 1997, 202. Altman, L. J.; Ash, L.; Marson, S. ibid. 1974, 129.
63. Eis, K.; Schmalz, H.-G. Synthesis 1997, 202. Altman, L. J.; Ash, L.; Marson, S. ibid. 1974, 129.
64. 10 by HPLC revealed the presence of the same 2-3% of a regioisomer.
65. Lipshutz, B. H.; Kim, S.-K.; Mollard, P.; Stevens, K. L. Tetrahedron 1998, 54, 6999.
66. Tamao, K.; Sumitani, K.; Kiso, Y.; Zembayashi, M.; Fujioka, A.; Kodama, S.; Nakajima, A.; Kumada, M. Bull. Chem. Soc. Jpn. 1976, 7, 1958. Tamao, K.; Kumada, M. In The Chemistry of the Metal-Carbon Bond; Hartley, F. R., Ed.; John Wiley: New York, 1987; Vol. 4, p 820.
67. Tamao, K.; Sumitani, K.; Kiso, Y.; Zembayashi, M.; Fujioka, A.; Kodama, S.; Nakajima, A.; Kumada, M. Bull. Chem. Soc. Jpn. 1976, 7, 1958. Tamao, K.; Kumada, M. In The Chemistry of the Metal-Carbon Bond; Hartley, F. R., Ed.; John Wiley: New York, 1987; Vol. 4, p 820.
68. Lipshutz, B. H.; Blomgren, P. A. J. Am. Chem. Soc. 1999, 121, 5819.
69. The corresponding bromomethylated p-quinone (36, X = Br) is known; cf. Niiro, Y.; Ueda, H.; Satoh, T.; Matsumoto, H. Japanese Patent WO 95-JP1621 950814.