The Friedel-Crafts allylation of a prenyl group stabilized by a sulfone moiety: Expeditious syntheses of ubiquinones and menaquinones

Journal of Organic Chemistry

Volumn 68, Issue 20, 2003, Pages 7925-7927

  Min, Jae Hong ^a   Lee, Jun Sup ^a   Yang, Jae Deuk ^a   Koo, Sangho ^a  

^a Myong Ji University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

FRIEDEL-CRAFTS ALLYLATION;

COENZYMES; SYNTHESIS (CHEMICAL);

AROMATIC COMPOUNDS;

FARNOQUINONE; MENAQUINONE; UBIDECARENONE; UBIQUINONE DERIVATIVE;

ALLYLATION; ARTICLE; CHEMICAL STRUCTURE; FRIEDEL CRAFTS REACTION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0141653948     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0350155     Document Type: Article

References (28)

1. (a) Thomson, R. H. Naturally Occurring Quinones; Academic Press: New York, 1971.
2. (b) Mitchell, P.; Moyle, J. Coenzyme Q; Lenaz, G., Ed.; Wiely: Chichester, UK, 1985.
3. Lenaz, G. Coenzyme Q, Biochemistry, Bioenergetics and Clinical Applications of Ubiquinone; Wiley-Interscience: New York, 1982.
4. (a) Lipshutz, B. H.; Kim, S.-K.; Mollard, P.; Stevens, K. L. Tetrahedron 1998, 1241.
5. (b) Lipshutz, B. H.; Bulow, G.; Fernandez-Lazaro, F.; Kim, S.-K.; Lowe, R.; Mollard, P.; Stevens, K. L. J. Am. Chem. Soc. 1999, 121, 11664.
6. (c) Lipshutz, B. H.; Mollard, P.; Pfeiffer, S. S.; Chrisman, W. J. Am. Chem. Soc. 2002, 124, 14282.
7. (d) van Liemt, W. B. S.; Steggerda, W. F.; Esmeijer, R.; Lugtenburg, J. Recl. Trav. Chim. Pays-Bas 1994, 113, 153.
8. (e) Inoue, S.; Yamaguchi, R.; Saito, K.; Sato, K. Bull. Chem. Soc. Jpn. 1974, 47, 3098.
9. (f) Garcías, X.; Ballester, P.; Capó, M.; Saá, J. M. J. Org. Chem. 1994, 59, 5093.
10. (g) Sato, K.; Inoue, S.; Saito, K. J. Chem. Soc., Perkin Trans. 1 1973, 2289.
11. (h) Snyder, C. D.; Rapoport, H. J. Am. Chem. Soc. 1974, 96, 8046
12. (i) Naruta, Y. J. Org. Chem. 1980, 45, 4097.
13. (a) Isler, O.; Rüegg, R.; Chopard-dit-Jean, L.; Winterstein, A.; Wiss, O. Helv. Chim. Acta 1958, 41, 786.
14. (b) Isler, O.; Doebel, K. Helv. Chim. Acta 1954, 37, 225.
15. (a) Hirschmann, R.; Miller, R.; Wendler, N. L. J. Am. Chem. Soc. 1954, 76, 4592.
16. (b) Araki, S.; Manabe, S.; Butsugan, Y. Chem. Lett. 1982, 797.
17. (a) Julia, M.; Arnould, D. Bull. Soc. Chim. Fr. 1973, 743.
18. (b) Julia, M.; Arnould, D. Bull. Soc. Chim. Fr. 1973, 7.46.
19. Terao, S.; Kato, K.; Shiraishi, M.; Morimoto, H. J. Org. Chem. 1979, 44, 868.
20. (a) Fujita, Y.; Ishiguro, M.; Onishi, T.; Nishida, T. Synthesis 1981, 469.
21. (b) Fujita, Y.; Ishiguro, M.; Onishi, T.; Nishida, T. Bull. Chem. Soc. Jpn. 1982, 55, 1325.
22. Keinan, E.; Eren, D. J. Org. Chem. 1987, 52, 3872.
23. Truce, W. E.; Goralski, C. T.; Christensen, L. W.; Bavry, R. H. J. Org. Chem. 1970, 35, 4217.
24. Olson, G. L.; Cheung, H.-C.; Morgan, K. D.; Neukom, C.; Saucy, G. J. Org. Chem. 1976, 41, 3287.
25. Tuyen, N. V.; Kesteleyn, B.; De Kimpe, N. Tetrahedron 2002, 58, 121.
26. Akkerman, J. M.; De Koning, H.; Huisman, H. O. J. Chem. Soc., Perkin Trans. 1 1979, 2124.
27. Mohri, M.; Kinoshita, H.; Inomata, K.; Kotake, H. Chem. Lett. 1985, 451.
28. Syper, L.; Kloc, K.; Mlochowski, J. Tetrahedron 1980, 36, 123.