A short, highly efficient synthesis of coenzyme Q10

Journal of the American Chemical Society

Volumn 124, Issue 48, 2002, Pages 14282-14283

  Lipshutz, Bruce H ^a   Mollard, Paul ^a   Pfeiffer, Steven S ^a   Chrisman, Will ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

UBIDECARENONE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; ENZYME SYNTHESIS; OXIDATION; REACTION ANALYSIS;

UBIQUINONE;

EID: 0037021499     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja021015v     Document Type: Article

References (47)

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3. Garrett, R. H.; Grisham, C. M. Biochemistry; Saunders College Publishing: Orlando, 1999. Stryer, L. Biochemistry; W. H. Freeman and Company: New York, 1995. Nelson, D. L.; Cox, M. M. Lehninger Principles of Biochemistry; Worth Publishers: New York, 2000.
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7. 10 Phenomenon; Keats Publishing: New Canaan, 1998. Coenzyme Q: Biochemistry, Bioenergetics, and Clinical Applications of Ubiquinone; Lenaz, G., Ed.; Wiley: New York, 1985. Coenzyme Q: Molecular Mechanisms in Health and Disease; Kagan, V. E., Quinn, P. J., Eds.; CRC Press: Boca Raton, FL, 2001.
8. Negishi, E.-I.; Liou, S.-Y.; Xu, C.; Huo, S. Org. Lett. 2002, 4, 261. Van Liemt, W. B. S.; Steggerda, W. F.; Esmeijer, R.; Lugtenburg, J. Recl. Trav. Chim. Pays-Bas 1994, 113, 153. Duralski, A. A.; Watts, A. Tetrahedron Lett. 1992, 33, 4983. Yanagisawa, A.; Nomura, N.; Nobuyoshi, N.; Noritake, Y.; Yamamoto, H. Synthesis 1991, 12, 1130. Rüttimann, A.; Lorenz, P. Helv. Chim. Acta 1990, 73, 790. Eren, D.; Keinan, E. J. Am. Chem. Soc. 1988, 110, 4356. Eto, H.; Eguchi, C. Chem. Lett. 1988, 1597. Mohri, M.; Kinoshita, H.; Inomata, K.; Kotake, H.; Takagaki, H.; Yamazaki, K. Chem. Lett. 1986, 1177. Sato, K.; Miyamoto, O.; Inoue, S.; Yamamoto, T.; Hirasawa, Y. J. Chem. Soc., Chem. Commun. 1982, 3, 153. Naruta, Y. J. Org. Chem. 1980, 45, 4097. Terao, S.; Kato, K.; Shiraishi, M.; Morimoto, H. J. Org. Chem. 1979, 44, 868. Terao, S.; Kato, K.; Shiraishi, M.; Morimoto, H. J. Chem. Soc., Perkin Trans. 1 1978, 10, 1101. Inoue, S.; Yamaguchi, R.; Saito, K.; Sato, K. Bull. Chem. Soc. Jpn. 1974, 47, 3098. Littaru, G. P.; Ho, L.; Folkers, K. Int. J. Vitam. Nutr. Res. 1972, 42, 291.
9. Negishi, E.-i.; Liou, S.-Y.; Xu, C.; Huo, S. Org. Lett. 2002, 4, 261. Van Liemt, W. B. S.; Steggerda, W. F.; Esmeijer, R.; Lugtenburg, J. Recl. Trav. Chim. Pays-Bas 1994, 113, 153. Duralski, A. A.; Watts, A. Tetrahedron Lett. 1992, 33, 4983. Yanagisawa, A.; Nomura, N.; Nobuyoshi, N.; Noritake, Y.; Yamamoto, H. Synthesis 1991, 12, 1130. Rüttimann, A.; Lorenz, P. Helv. Chim. Acta 1990, 73, 790. Eren, D.; Keinan, E. J. Am. Chem. Soc. 1988, 110, 4356. Eto, H.; Eguchi, C. Chem. Lett. 1988, 1597. Mohri, M.; Kinoshita, H.; Inomata, K.; Kotake, H.; Takagaki, H.; Yamazaki, K. Chem. Lett. 1986, 1177. Sato, K.; Miyamoto, O.; Inoue, S.; Yamamoto, T.; Hirasawa, Y. J. Chem. Soc., Chem. Commun. 1982, 3, 153. Naruta, Y. J. Org. Chem. 1980, 45, 4097. Terao, S.; Kato, K.; Shiraishi, M.; Morimoto, H. J. Org. Chem. 1979, 44, 868. Terao, S.; Kato, K.; Shiraishi, M.; Morimoto, H. J. Chem. Soc., Perkin Trans. 1 1978, 10, 1101. Inoue, S.; Yamaguchi, R.; Saito, K.; Sato, K. Bull. Chem. Soc. Jpn. 1974, 47, 3098. Littaru, G. P.; Ho, L.; Folkers, K. Int. J. Vitam. Nutr. Res. 1972, 42, 291.
10. Negishi, E.-i.; Liou, S.-Y.; Xu, C.; Huo, S. Org. Lett. 2002, 4, 261. Van Liemt, W. B. S.; Steggerda, W. F.; Esmeijer, R.; Lugtenburg, J. Recl. Trav. Chim. Pays-Bas 1994, 113, 153. Duralski, A. A.; Watts, A. Tetrahedron Lett. 1992, 33, 4983. Yanagisawa, A.; Nomura, N.; Nobuyoshi, N.; Noritake, Y.; Yamamoto, H. Synthesis 1991, 12, 1130. Rüttimann, A.; Lorenz, P. Helv. Chim. Acta 1990, 73, 790. Eren, D.; Keinan, E. J. Am. Chem. Soc. 1988, 110, 4356. Eto, H.; Eguchi, C. Chem. Lett. 1988, 1597. Mohri, M.; Kinoshita, H.; Inomata, K.; Kotake, H.; Takagaki, H.; Yamazaki, K. Chem. Lett. 1986, 1177. Sato, K.; Miyamoto, O.; Inoue, S.; Yamamoto, T.; Hirasawa, Y. J. Chem. Soc., Chem. Commun. 1982, 3, 153. Naruta, Y. J. Org. Chem. 1980, 45, 4097. Terao, S.; Kato, K.; Shiraishi, M.; Morimoto, H. J. Org. Chem. 1979, 44, 868. Terao, S.; Kato, K.; Shiraishi, M.; Morimoto, H. J. Chem. Soc., Perkin Trans. 1 1978, 10, 1101. Inoue, S.; Yamaguchi, R.; Saito, K.; Sato, K. Bull. Chem. Soc. Jpn. 1974, 47, 3098. Littaru, G. P.; Ho, L.; Folkers, K. Int. J. Vitam. Nutr. Res. 1972, 42, 291.
11. Negishi, E.-i.; Liou, S.-Y.; Xu, C.; Huo, S. Org. Lett. 2002, 4, 261. Van Liemt, W. B. S.; Steggerda, W. F.; Esmeijer, R.; Lugtenburg, J. Recl. Trav. Chim. Pays-Bas 1994, 113, 153. Duralski, A. A.; Watts, A. Tetrahedron Lett. 1992, 33, 4983. Yanagisawa, A.; Nomura, N.; Nobuyoshi, N.; Noritake, Y.; Yamamoto, H. Synthesis 1991, 12, 1130. Rüttimann, A.; Lorenz, P. Helv. Chim. Acta 1990, 73, 790. Eren, D.; Keinan, E. J. Am. Chem. Soc. 1988, 110, 4356. Eto, H.; Eguchi, C. Chem. Lett. 1988, 1597. Mohri, M.; Kinoshita, H.; Inomata, K.; Kotake, H.; Takagaki, H.; Yamazaki, K. Chem. Lett. 1986, 1177. Sato, K.; Miyamoto, O.; Inoue, S.; Yamamoto, T.; Hirasawa, Y. J. Chem. Soc., Chem. Commun. 1982, 3, 153. Naruta, Y. J. Org. Chem. 1980, 45, 4097. Terao, S.; Kato, K.; Shiraishi, M.; Morimoto, H. J. Org. Chem. 1979, 44, 868. Terao, S.; Kato, K.; Shiraishi, M.; Morimoto, H. J. Chem. Soc., Perkin Trans. 1 1978, 10, 1101. Inoue, S.; Yamaguchi, R.; Saito, K.; Sato, K. Bull. Chem. Soc. Jpn. 1974, 47, 3098. Littaru, G. P.; Ho, L.; Folkers, K. Int. J. Vitam. Nutr. Res. 1972, 42, 291.
12. Negishi, E.-i.; Liou, S.-Y.; Xu, C.; Huo, S. Org. Lett. 2002, 4, 261. Van Liemt, W. B. S.; Steggerda, W. F.; Esmeijer, R.; Lugtenburg, J. Recl. Trav. Chim. Pays-Bas 1994, 113, 153. Duralski, A. A.; Watts, A. Tetrahedron Lett. 1992, 33, 4983. Yanagisawa, A.; Nomura, N.; Nobuyoshi, N.; Noritake, Y.; Yamamoto, H. Synthesis 1991, 12, 1130. Rüttimann, A.; Lorenz, P. Helv. Chim. Acta 1990, 73, 790. Eren, D.; Keinan, E. J. Am. Chem. Soc. 1988, 110, 4356. Eto, H.; Eguchi, C. Chem. Lett. 1988, 1597. Mohri, M.; Kinoshita, H.; Inomata, K.; Kotake, H.; Takagaki, H.; Yamazaki, K. Chem. Lett. 1986, 1177. Sato, K.; Miyamoto, O.; Inoue, S.; Yamamoto, T.; Hirasawa, Y. J. Chem. Soc., Chem. Commun. 1982, 3, 153. Naruta, Y. J. Org. Chem. 1980, 45, 4097. Terao, S.; Kato, K.; Shiraishi, M.; Morimoto, H. J. Org. Chem. 1979, 44, 868. Terao, S.; Kato, K.; Shiraishi, M.; Morimoto, H. J. Chem. Soc., Perkin Trans. 1 1978, 10, 1101. Inoue, S.; Yamaguchi, R.; Saito, K.; Sato, K. Bull. Chem. Soc. Jpn. 1974, 47, 3098. Littaru, G. P.; Ho, L.; Folkers, K. Int. J. Vitam. Nutr. Res. 1972, 42, 291.
13. Negishi, E.-i.; Liou, S.-Y.; Xu, C.; Huo, S. Org. Lett. 2002, 4, 261. Van Liemt, W. B. S.; Steggerda, W. F.; Esmeijer, R.; Lugtenburg, J. Recl. Trav. Chim. Pays-Bas 1994, 113, 153. Duralski, A. A.; Watts, A. Tetrahedron Lett. 1992, 33, 4983. Yanagisawa, A.; Nomura, N.; Nobuyoshi, N.; Noritake, Y.; Yamamoto, H. Synthesis 1991, 12, 1130. Rüttimann, A.; Lorenz, P. Helv. Chim. Acta 1990, 73, 790. Eren, D.; Keinan, E. J. Am. Chem. Soc. 1988, 110, 4356. Eto, H.; Eguchi, C. Chem. Lett. 1988, 1597. Mohri, M.; Kinoshita, H.; Inomata, K.; Kotake, H.; Takagaki, H.; Yamazaki, K. Chem. Lett. 1986, 1177. Sato, K.; Miyamoto, O.; Inoue, S.; Yamamoto, T.; Hirasawa, Y. J. Chem. Soc., Chem. Commun. 1982, 3, 153. Naruta, Y. J. Org. Chem. 1980, 45, 4097. Terao, S.; Kato, K.; Shiraishi, M.; Morimoto, H. J. Org. Chem. 1979, 44, 868. Terao, S.; Kato, K.; Shiraishi, M.; Morimoto, H. J. Chem. Soc., Perkin Trans. 1 1978, 10, 1101. Inoue, S.; Yamaguchi, R.; Saito, K.; Sato, K. Bull. Chem. Soc. Jpn. 1974, 47, 3098. Littaru, G. P.; Ho, L.; Folkers, K. Int. J. Vitam. Nutr. Res. 1972, 42, 291.
14. Negishi, E.-i.; Liou, S.-Y.; Xu, C.; Huo, S. Org. Lett. 2002, 4, 261. Van Liemt, W. B. S.; Steggerda, W. F.; Esmeijer, R.; Lugtenburg, J. Recl. Trav. Chim. Pays-Bas 1994, 113, 153. Duralski, A. A.; Watts, A. Tetrahedron Lett. 1992, 33, 4983. Yanagisawa, A.; Nomura, N.; Nobuyoshi, N.; Noritake, Y.; Yamamoto, H. Synthesis 1991, 12, 1130. Rüttimann, A.; Lorenz, P. Helv. Chim. Acta 1990, 73, 790. Eren, D.; Keinan, E. J. Am. Chem. Soc. 1988, 110, 4356. Eto, H.; Eguchi, C. Chem. Lett. 1988, 1597. Mohri, M.; Kinoshita, H.; Inomata, K.; Kotake, H.; Takagaki, H.; Yamazaki, K. Chem. Lett. 1986, 1177. Sato, K.; Miyamoto, O.; Inoue, S.; Yamamoto, T.; Hirasawa, Y. J. Chem. Soc., Chem. Commun. 1982, 3, 153. Naruta, Y. J. Org. Chem. 1980, 45, 4097. Terao, S.; Kato, K.; Shiraishi, M.; Morimoto, H. J. Org. Chem. 1979, 44, 868. Terao, S.; Kato, K.; Shiraishi, M.; Morimoto, H. J. Chem. Soc., Perkin Trans. 1 1978, 10, 1101. Inoue, S.; Yamaguchi, R.; Saito, K.; Sato, K. Bull. Chem. Soc. Jpn. 1974, 47, 3098. Littaru, G. P.; Ho, L.; Folkers, K. Int. J. Vitam. Nutr. Res. 1972, 42, 291.
15. Negishi, E.-i.; Liou, S.-Y.; Xu, C.; Huo, S. Org. Lett. 2002, 4, 261. Van Liemt, W. B. S.; Steggerda, W. F.; Esmeijer, R.; Lugtenburg, J. Recl. Trav. Chim. Pays-Bas 1994, 113, 153. Duralski, A. A.; Watts, A. Tetrahedron Lett. 1992, 33, 4983. Yanagisawa, A.; Nomura, N.; Nobuyoshi, N.; Noritake, Y.; Yamamoto, H. Synthesis 1991, 12, 1130. Rüttimann, A.; Lorenz, P. Helv. Chim. Acta 1990, 73, 790. Eren, D.; Keinan, E. J. Am. Chem. Soc. 1988, 110, 4356. Eto, H.; Eguchi, C. Chem. Lett. 1988, 1597. Mohri, M.; Kinoshita, H.; Inomata, K.; Kotake, H.; Takagaki, H.; Yamazaki, K. Chem. Lett. 1986, 1177. Sato, K.; Miyamoto, O.; Inoue, S.; Yamamoto, T.; Hirasawa, Y. J. Chem. Soc., Chem. Commun. 1982, 3, 153. Naruta, Y. J. Org. Chem. 1980, 45, 4097. Terao, S.; Kato, K.; Shiraishi, M.; Morimoto, H. J. Org. Chem. 1979, 44, 868. Terao, S.; Kato, K.; Shiraishi, M.; Morimoto, H. J. Chem. Soc., Perkin Trans. 1 1978, 10, 1101. Inoue, S.; Yamaguchi, R.; Saito, K.; Sato, K. Bull. Chem. Soc. Jpn. 1974, 47, 3098. Littaru, G. P.; Ho, L.; Folkers, K. Int. J. Vitam. Nutr. Res. 1972, 42, 291.
16. Negishi, E.-i.; Liou, S.-Y.; Xu, C.; Huo, S. Org. Lett. 2002, 4, 261. Van Liemt, W. B. S.; Steggerda, W. F.; Esmeijer, R.; Lugtenburg, J. Recl. Trav. Chim. Pays-Bas 1994, 113, 153. Duralski, A. A.; Watts, A. Tetrahedron Lett. 1992, 33, 4983. Yanagisawa, A.; Nomura, N.; Nobuyoshi, N.; Noritake, Y.; Yamamoto, H. Synthesis 1991, 12, 1130. Rüttimann, A.; Lorenz, P. Helv. Chim. Acta 1990, 73, 790. Eren, D.; Keinan, E. J. Am. Chem. Soc. 1988, 110, 4356. Eto, H.; Eguchi, C. Chem. Lett. 1988, 1597. Mohri, M.; Kinoshita, H.; Inomata, K.; Kotake, H.; Takagaki, H.; Yamazaki, K. Chem. Lett. 1986, 1177. Sato, K.; Miyamoto, O.; Inoue, S.; Yamamoto, T.; Hirasawa, Y. J. Chem. Soc., Chem. Commun. 1982, 3, 153. Naruta, Y. J. Org. Chem. 1980, 45, 4097. Terao, S.; Kato, K.; Shiraishi, M.; Morimoto, H. J. Org. Chem. 1979, 44, 868. Terao, S.; Kato, K.; Shiraishi, M.; Morimoto, H. J. Chem. Soc., Perkin Trans. 1 1978, 10, 1101. Inoue, S.; Yamaguchi, R.; Saito, K.; Sato, K. Bull. Chem. Soc. Jpn. 1974, 47, 3098. Littaru, G. P.; Ho, L.; Folkers, K. Int. J. Vitam. Nutr. Res. 1972, 42, 291.
17. Negishi, E.-i.; Liou, S.-Y.; Xu, C.; Huo, S. Org. Lett. 2002, 4, 261. Van Liemt, W. B. S.; Steggerda, W. F.; Esmeijer, R.; Lugtenburg, J. Recl. Trav. Chim. Pays-Bas 1994, 113, 153. Duralski, A. A.; Watts, A. Tetrahedron Lett. 1992, 33, 4983. Yanagisawa, A.; Nomura, N.; Nobuyoshi, N.; Noritake, Y.; Yamamoto, H. Synthesis 1991, 12, 1130. Rüttimann, A.; Lorenz, P. Helv. Chim. Acta 1990, 73, 790. Eren, D.; Keinan, E. J. Am. Chem. Soc. 1988, 110, 4356. Eto, H.; Eguchi, C. Chem. Lett. 1988, 1597. Mohri, M.; Kinoshita, H.; Inomata, K.; Kotake, H.; Takagaki, H.; Yamazaki, K. Chem. Lett. 1986, 1177. Sato, K.; Miyamoto, O.; Inoue, S.; Yamamoto, T.; Hirasawa, Y. J. Chem. Soc., Chem. Commun. 1982, 3, 153. Naruta, Y. J. Org. Chem. 1980, 45, 4097. Terao, S.; Kato, K.; Shiraishi, M.; Morimoto, H. J. Org. Chem. 1979, 44, 868. Terao, S.; Kato, K.; Shiraishi, M.; Morimoto, H. J. Chem. Soc., Perkin Trans. 1 1978, 10, 1101. Inoue, S.; Yamaguchi, R.; Saito, K.; Sato, K. Bull. Chem. Soc. Jpn. 1974, 47, 3098. Littaru, G. P.; Ho, L.; Folkers, K. Int. J. Vitam. Nutr. Res. 1972, 42, 291.
18. Negishi, E.-i.; Liou, S.-Y.; Xu, C.; Huo, S. Org. Lett. 2002, 4, 261. Van Liemt, W. B. S.; Steggerda, W. F.; Esmeijer, R.; Lugtenburg, J. Recl. Trav. Chim. Pays-Bas 1994, 113, 153. Duralski, A. A.; Watts, A. Tetrahedron Lett. 1992, 33, 4983. Yanagisawa, A.; Nomura, N.; Nobuyoshi, N.; Noritake, Y.; Yamamoto, H. Synthesis 1991, 12, 1130. Rüttimann, A.; Lorenz, P. Helv. Chim. Acta 1990, 73, 790. Eren, D.; Keinan, E. J. Am. Chem. Soc. 1988, 110, 4356. Eto, H.; Eguchi, C. Chem. Lett. 1988, 1597. Mohri, M.; Kinoshita, H.; Inomata, K.; Kotake, H.; Takagaki, H.; Yamazaki, K. Chem. Lett. 1986, 1177. Sato, K.; Miyamoto, O.; Inoue, S.; Yamamoto, T.; Hirasawa, Y. J. Chem. Soc., Chem. Commun. 1982, 3, 153. Naruta, Y. J. Org. Chem. 1980, 45, 4097. Terao, S.; Kato, K.; Shiraishi, M.; Morimoto, H. J. Org. Chem. 1979, 44, 868. Terao, S.; Kato, K.; Shiraishi, M.; Morimoto, H. J. Chem. Soc., Perkin Trans. 1 1978, 10, 1101. Inoue, S.; Yamaguchi, R.; Saito, K.; Sato, K. Bull. Chem. Soc. Jpn. 1974, 47, 3098. Littaru, G. P.; Ho, L.; Folkers, K. Int. J. Vitam. Nutr. Res. 1972, 42, 291.
19. Negishi, E.-i.; Liou, S.-Y.; Xu, C.; Huo, S. Org. Lett. 2002, 4, 261. Van Liemt, W. B. S.; Steggerda, W. F.; Esmeijer, R.; Lugtenburg, J. Recl. Trav. Chim. Pays-Bas 1994, 113, 153. Duralski, A. A.; Watts, A. Tetrahedron Lett. 1992, 33, 4983. Yanagisawa, A.; Nomura, N.; Nobuyoshi, N.; Noritake, Y.; Yamamoto, H. Synthesis 1991, 12, 1130. Rüttimann, A.; Lorenz, P. Helv. Chim. Acta 1990, 73, 790. Eren, D.; Keinan, E. J. Am. Chem. Soc. 1988, 110, 4356. Eto, H.; Eguchi, C. Chem. Lett. 1988, 1597. Mohri, M.; Kinoshita, H.; Inomata, K.; Kotake, H.; Takagaki, H.; Yamazaki, K. Chem. Lett. 1986, 1177. Sato, K.; Miyamoto, O.; Inoue, S.; Yamamoto, T.; Hirasawa, Y. J. Chem. Soc., Chem. Commun. 1982, 3, 153. Naruta, Y. J. Org. Chem. 1980, 45, 4097. Terao, S.; Kato, K.; Shiraishi, M.; Morimoto, H. J. Org. Chem. 1979, 44, 868. Terao, S.; Kato, K.; Shiraishi, M.; Morimoto, H. J. Chem. Soc., Perkin Trans. 1 1978, 10, 1101. Inoue, S.; Yamaguchi, R.; Saito, K.; Sato, K. Bull. Chem. Soc. Jpn. 1974, 47, 3098. Littaru, G. P.; Ho, L.; Folkers, K. Int. J. Vitam. Nutr. Res. 1972, 42, 291.
20. Negishi, E.-i.; Liou, S.-Y.; Xu, C.; Huo, S. Org. Lett. 2002, 4, 261. Van Liemt, W. B. S.; Steggerda, W. F.; Esmeijer, R.; Lugtenburg, J. Recl. Trav. Chim. Pays-Bas 1994, 113, 153. Duralski, A. A.; Watts, A. Tetrahedron Lett. 1992, 33, 4983. Yanagisawa, A.; Nomura, N.; Nobuyoshi, N.; Noritake, Y.; Yamamoto, H. Synthesis 1991, 12, 1130. Rüttimann, A.; Lorenz, P. Helv. Chim. Acta 1990, 73, 790. Eren, D.; Keinan, E. J. Am. Chem. Soc. 1988, 110, 4356. Eto, H.; Eguchi, C. Chem. Lett. 1988, 1597. Mohri, M.; Kinoshita, H.; Inomata, K.; Kotake, H.; Takagaki, H.; Yamazaki, K. Chem. Lett. 1986, 1177. Sato, K.; Miyamoto, O.; Inoue, S.; Yamamoto, T.; Hirasawa, Y. J. Chem. Soc., Chem. Commun. 1982, 3, 153. Naruta, Y. J. Org. Chem. 1980, 45, 4097. Terao, S.; Kato, K.; Shiraishi, M.; Morimoto, H. J. Org. Chem. 1979, 44, 868. Terao, S.; Kato, K.; Shiraishi, M.; Morimoto, H. J. Chem. Soc., Perkin Trans. 1 1978, 10, 1101. Inoue, S.; Yamaguchi, R.; Saito, K.; Sato, K. Bull. Chem. Soc. Jpn. 1974, 47, 3098. Littaru, G. P.; Ho, L.; Folkers, K. Int. J. Vitam. Nutr. Res. 1972, 42, 291.
21. Negishi, E.-i.; Liou, S.-Y.; Xu, C.; Huo, S. Org. Lett. 2002, 4, 261. Van Liemt, W. B. S.; Steggerda, W. F.; Esmeijer, R.; Lugtenburg, J. Recl. Trav. Chim. Pays-Bas 1994, 113, 153. Duralski, A. A.; Watts, A. Tetrahedron Lett. 1992, 33, 4983. Yanagisawa, A.; Nomura, N.; Nobuyoshi, N.; Noritake, Y.; Yamamoto, H. Synthesis 1991, 12, 1130. Rüttimann, A.; Lorenz, P. Helv. Chim. Acta 1990, 73, 790. Eren, D.; Keinan, E. J. Am. Chem. Soc. 1988, 110, 4356. Eto, H.; Eguchi, C. Chem. Lett. 1988, 1597. Mohri, M.; Kinoshita, H.; Inomata, K.; Kotake, H.; Takagaki, H.; Yamazaki, K. Chem. Lett. 1986, 1177. Sato, K.; Miyamoto, O.; Inoue, S.; Yamamoto, T.; Hirasawa, Y. J. Chem. Soc., Chem. Commun. 1982, 3, 153. Naruta, Y. J. Org. Chem. 1980, 45, 4097. Terao, S.; Kato, K.; Shiraishi, M.; Morimoto, H. J. Org. Chem. 1979, 44, 868. Terao, S.; Kato, K.; Shiraishi, M.; Morimoto, H. J. Chem. Soc., Perkin Trans. 1 1978, 10, 1101. Inoue, S.; Yamaguchi, R.; Saito, K.; Sato, K. Bull. Chem. Soc. Jpn. 1974, 47, 3098. Littaru, G. P.; Ho, L.; Folkers, K. Int. J. Vitam. Nutr. Res. 1972, 42, 291.
22. Lipshutz, B. H.; Kim, S.-K.; Mollard, P.; Stevens, K. L. Tetrahedron 1998, 54(7), 1241. Rüttimann, A.; Lorenz, P. Helv. Chim. Acta 1990, 73, 790. Araki, S.; Sato, T.; Miyagawa, H.; Butsugan, Y. Bull. Chem. Soc. Jpn. 1984, 57, 3523. Sato, K.; Inoue, S.; Sato, H. Bull. Chem. Soc. Jpn. 1972, 45, 3455. Shunk, C. H.; Erickson, R. E.; Wong, E. L.; Folkers, K. J. Am. Chem. Soc. 1959, 81, 5000.
23. Lipshutz, B. H.; Kim, S.-K.; Mollard, P.; Stevens, K. L. Tetrahedron 1998, 54(7), 1241. Rüttimann, A.; Lorenz, P. Helv. Chim. Acta 1990, 73, 790. Araki, S.; Sato, T.; Miyagawa, H.; Butsugan, Y. Bull. Chem. Soc. Jpn. 1984, 57, 3523. Sato, K.; Inoue, S.; Sato, H. Bull. Chem. Soc. Jpn. 1972, 45, 3455. Shunk, C. H.; Erickson, R. E.; Wong, E. L.; Folkers, K. J. Am. Chem. Soc. 1959, 81, 5000.
24. Lipshutz, B. H.; Kim, S.-K.; Mollard, P.; Stevens, K. L. Tetrahedron 1998, 54(7), 1241. Rüttimann, A.; Lorenz, P. Helv. Chim. Acta 1990, 73, 790. Araki, S.; Sato, T.; Miyagawa, H.; Butsugan, Y. Bull. Chem. Soc. Jpn. 1984, 57, 3523. Sato, K.; Inoue, S.; Sato, H. Bull. Chem. Soc. Jpn. 1972, 45, 3455. Shunk, C. H.; Erickson, R. E.; Wong, E. L.; Folkers, K. J. Am. Chem. Soc. 1959, 81, 5000.
25. Lipshutz, B. H.; Kim, S.-K.; Mollard, P.; Stevens, K. L. Tetrahedron 1998, 54(7), 1241. Rüttimann, A.; Lorenz, P. Helv. Chim. Acta 1990, 73, 790. Araki, S.; Sato, T.; Miyagawa, H.; Butsugan, Y. Bull. Chem. Soc. Jpn. 1984, 57, 3523. Sato, K.; Inoue, S.; Sato, H. Bull. Chem. Soc. Jpn. 1972, 45, 3455. Shunk, C. H.; Erickson, R. E.; Wong, E. L.; Folkers, K. J. Am. Chem. Soc. 1959, 81, 5000.
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