A short catalytic enantioselective synthesis of the proinflammatory eicosanoid 12(R)-hydroxy-5(Z),8(Z),10(E),14(Z)-eicosatetraenoic acid (12(R)-HETE)

Organic Letters

Volumn 2, Issue 16, 2000, Pages 2543-2544

  Han, Xiaojun ^a   Corey, E J ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

12 HYDROXYICOSATETRAENOIC ACID; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; STEREOISOMERISM; SYNTHESIS;

12-HYDROXY-5,8,10,14-EICOSATETRAENOIC ACID; INDICATORS AND REAGENTS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; STEREOISOMERISM;

EID: 0034632357     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0062392     Document Type: Article

References (41)

1. Hamberg, M.; Samuelsson, B. Proc. Natl. Acad. Sci. U.S.A. 1974, 71, 3400.
2. Hammarström, S.; Hamberg, M.; Samuelsson, B.; Duell, E. A.; Stawiski, M.; Voorhees, J. J. Proc. Natl. Acad. Sci. U.S.A. 1975, 72, 5130.
3. (a) Nie, D.; Tang, K.; Diglio, C.; Honn, K. V. Blood 2000, 95, 2304.
4. (b) Tang, K.; Finley, R. L.; Nie, D.; Honn, K. V. Biochemistry 2000, 39, 3185.
5. Nie, D.; Hillman, G. G.; Geddes, T.; Tang, K.; Pierson, C; Grignon, D. J.; Honn, K. V. Adv. Exptl. Med. Biol. 1999, 469, 623.
6. (a) Ding, X. Z.; Iversen, P.; Cluck, M. W.; Knezetic, J. A.; Adrian, T. E. Biochem. Biophys. Res. Commun. 1999, 261, 218.
7. (b) Chen, L. C.; Chen, B. K.; Liu, Y.W.; Chang, W. C. FEBS Lett. 1999, 455, 105.
8. Tang, K.; Honn, K. V. Adv. Exptl. Med. Biol. 1999, 447, 181.
9. Yamamoto, S.; Suzuki H.; Ueda, N. Prog. Lipid Res. 1997, 36, 23.
10. (e) Herbertsson, H.; Hammarström, S. Adv. Exptl. Med. Biol. 1997, 400A, 287.
11. (f) Nie, D.; Hillman, G. G.; Geddes, T.; Tang, K.; Pierson, C.; Grignon, D. J.; Honn, K. V. Cancer Res. 1998, 58, 4047.
12. Cyrus, T.; Witztum, J. L.; Rader, D. J.; Tangirala, R.; Fazio, S.; Linton, M. F.; Funk, C. D. J. Clin. Invest. 1993, 103, 1597.
13. Katoh, A.; Ikeda, H.; Murohara, T.; Haramaki, N.; Ito, H.; Imaizumi, T. Circulation 1998, 98, 2891.
14. Bleich, D.; Chen, S.; Zipser, B.; Sun, D.; Funk, C. D.; Nadler, J. L. J. Clin. Invest. 1999, 103, 1431.
15. (a) Ziboh, V. A. Lipids 1996, 31, S249.
16. (b) Natarajan, R.; Pei, H.; Gu, J. L.; Sarma, J. M.; Nadler, J. Cardiovasc. Res. 1999, 41, 489.
17. Tang, D. G.; Chen, Y. Q.; Honn, K. V. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 5241.
18. (a) Woolard, P. M. Biochem. Biophys. Res. Commun. 1986, 136, 169.
19. (b) Cunningham, F. M.; Woolard, P. M. Prostaglandins 1987, 34, 71.
20. (a) Boeglin, W. E.; Kim, R. B.; Brash, A. R. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 6744.
21. (b) Sun, D.; McDonnell, M.; Chen, X. S.; Lakkis, M. M.; Li, H.; Isaacs, S. N.; Elsea, S. H.; Patel, P. I.; Funk, C. D. J. Biol. Chem. 1998, 273, 33540.
22. (a) Izumi, T.; Hoshiko, S.; Rådmark, O.; Samuelsson, B. Proc. Natl. Acad. Sci. U.S.A. 1990, 87, 7477.
23. (b) Funk, C. D.; Furci, L.; Fitzgerald, G. A. Proc. Natl. Acad. Sci. U.S.A. 1990, 87, 5638.
24. Corey, E. J.; Niwa, H.; Knolle, J. J. Am. Chem. Soc. 1978, 100, 1942.
25. (a) Corey, E. J.; Marfat, A.; Falck, J. R.; Albright, J. O. J. Am. Chem. Soc. 1980, 102, 1433.
26. (b) Corey, E. J.; Kyler, K.; Raju, N. Tetrahedron Lett. 1984, 25, 5115.
27. Russell, S. W.; Pabon, H. J. J. J. Chem. Soc., Perkin Trans. 1 1982, 545.
28. Just, G.; Wang, Z. Y. Tetrahedron Lett. 1985, 26, 2993.
29. (e) Just, G.; Wang, Z. Y. J. Org. Chem. 1986, 51, 4796.
30. (f) Yadagiri, P.; Lumin, S.; Mosset, P.; Capdevila, J.; Falck, J. R. Tetrahedron Lett. 1986, 27, 6039.
31. (g) Shimazaki, T.; Kobayashi, Y.; Sato, F. Chem. Lett. 1988, 1785.
32. (h) Nagata, R.; Kawakami, M.; Matsuura, T.; Saito, I. Tetrahedron Lett. 1989, 30, 2817.
33. Nicolaou, K. C.; Ramphal, J. Y.; Abe, Y. Synthesis 1989, 898.
34. (j) Mosset, P.; Pointeau, P.; Aubert, F.; Lellouche, J. P.; Beaucourt, J. P.; Grée, R. Bull. Soc. Chim. Fr. 1990, 127, 298.
35. (k) Lumin, S.; Falck, J. R.; Schwartzman, M. L. Tetrahedron Lett. 1991, 32, 2315.
36. Nicolaou, K. C.; Ladduwahetty, T.; Elisseou, E. M. J. Chem. Soc., Chem. Commun. 1985, 1580.
37. Kiji, J.; Okano, T.; Higashimae, Y.; Fukui, Y. Bull. Chem. Soc. Jpn. 1996, 69, 1029. Increased pressure of CO minimizes methanolysis of allylic bromide 3 to the corresponding methyl ether.
38. (a) Sharpless, K. B.; Amberg, W.; Bennani, Y.; Crispino, G. A.; Hartung, J.; Jeong, K.-S.; Kwong, H.-L.; Morikawa, K.; Wang, Z.-M.; Xu, D.; Zhang, X.-L. J. Org. Chem. 1992, 57, 2768.
39. (b) Wang, Z.; Zhang, X.; Sharpless, K. B.; Sinha, S. C.; Sinha-Bagchi, A.; Keinan, E. Tetrahedron Lett. 1992, 33, 6407.
40. Ylide 8 was prepared from the corresponding phosphonium salt by reaction with sodium hexamethyldisilazide in THF at -25 °C, see: (a) Zamboni, R.; Milette, S.; Rokach, J. Tetrahedron Lett. 1983, 24, 4899.
41. (b) Sandri, J.; Viala, J. J. Org. Chem. 1995, 60, 6627.