A cross-metathesis route to the 5-F2-isoprostanes

Journal of Organic Chemistry

Volumn 73, Issue 10, 2008, Pages 3754-3758

  Pandya, Bhaumik A ^a   Snapper, Marc L ^a  

^a BOSTON COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ENANTIOMERS; ETHYLENE; KETONES; METABOLITES; REGIOSELECTIVITY; STEREOSELECTIVITY;

ALLYLIC ALCOHOLS; GLOBAL DEPROTECTION; ISOPROSTANES; RACEMIC ENONES; STEREODIVERGENT ROUTE;

AROMATIC HYDROCARBONS;

ARACHIDONIC ACID; BICYCLO[3.2.0]HEPTANE DERIVATIVE; CYCLOPENTENONE DERIVATIVE; ETHYLENE; ISOPROSTANE DERIVATIVE; KETONE;

ARTICLE; CATALYST; CHEMICAL STRUCTURE; HYDROBORATION; LIPID OXIDATION; POLYMERIZATION; REDUCTION; RING CLOSING METATHESIS; RING OPENING;

ISOPROSTANES; MOLECULAR CONFORMATION; STEREOISOMERISM;

EID: 43449101207     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo702702s     Document Type: Article

References (59)

1. For heptatorenal syndrome, see: (a) Morrow, J. D.; Moore, K. P.; Awad, J. A.; Raveenscraft, M. D.; Marini, G.; Badr, K. F.; Williams, R.; Roberts, L. J, II. Lipid Mediators 1993, 6, 417.
2. For alcohol induced-liver disease, see: (b) Lands, W. E. Alcohol.: Clin. Exp. Res. 1995, 19, 928.
3. For pulmonary hypertension, see: (c) Kang, H. K.; Morrow, J. D.; Roberts, L. J., II; Newman, J. H.; Banerjee, M. J. Appl. Physiol. 1993, 74, 460.
4. For myocardial infarction, see: (d) Sing, N.; Dhalla, A. K.; Seneviratne, C.; Singal, P. K. Mol. Cell. Biochem. 1995, 147, 77.
5. For atherosclerosis, see: (e) Gopaul, N. K.; Nourooz-Zadeh, J.; Mallet, A. I.; Anggard, E. E. Biochem. Biophys. Res. Commun. 1994, 200, 338.
6. (f) Cracowski, J.-L. Chem. Phys. Lipids 2004, 128, 75.
7. For example, see: (a) Prostaglandins, Leukotrienes and Essential Fatty Acids; Horrobin, D. F., Manku, M. S., Sirois, P., Borgeat, P., Eds.; Churchill Livingstone: Edinburgh, UK, 2002.
8. (b) Prostaglandins, leukotrienes and other eicosanoids: from biogenesis to clinical application, Marks, F., Furstenberger, G., Eds.; Wiley-VCH: Weinheim, Germany, 1999.
9. Also see: (c) Helmer, M. E.; Lands, W. E. M. Lipids 1997, 12, 591.
10. (d) Porter, N. A.; Funk, M. O. J. Org. Chem. 1975, 40, 3614.
11. Shizuka, M.; Schrader, T. O.; Snapper, M. L. J. Org. Chem. 2006, 71, 1330.
12. Morrow, J. D.; Hill, K. E.; Burk, R. F.; Nammour, T. M.; Badr, K. F.; Roberts, L. J., II. Proc. Natl. Acad. Sci. U.S.A. 1990, 87, 9383.
13. (a) Garret, A. F.; Rokach, J.; Lawson, J. A.; Patrico, D. Chem. Phys. Lipids 2004, 128, 165.
14. (b) Morrow, J. D.; Roberts, L. J., II. Cell. Mol. Life Sci. 2002, 59, 808.
15. (c) Lawson, J. A.; Rokach, J.; Fitzgerald, G. A. J. Biol. Chem. 1999, 274, 2441.
16. (d) Lawson, J. A.; Li, H.; Rokach, J.; Adiyaman, M.; Hwang, S. W.; Khanapure, S. P.; Fitzgerald, G. A. J. Biol. Chem. 1998, 273, 29295.
17. (e) Kadiiska, M. B.; Morrow, J. D.; Awad, J. A.; Roberts, L. J., II; Mason, R. P. Chem. Res. Toxicol. 1998, 11, 1516.
18. (f) Morrow, J. D.; Minton, T. A.; Mukundan, C. R.; Campbell, M. D.; Zackert, W. E.; Daniel, V. C.; Badr, K. F.; Blair, I. A.; Roberts, L. J., II. J. Biol. Chem. 1994, 269, 4317.
19. Hou, X.; Roberts, L. J., II; Gobeil, F., Jr.; Taber, D. F.; Kanai, K.; Abran, D.; Brault, S.; Daniella, C.; Sennlaub, F.; LaChapelle, P.; Varma, D. R.; Chemtob, S. Free Radical Bio. Med. 2004, 36, 163.
20. Adiyaman, M.; Lawson, J. A.; Hwang, S.-W.; Khanapure, S. P.; FitzGerald, G. A.; Rokach, J. Tetrahedron Lett. 1996, 37, 4849.
21. (a) Morrow, J. D.; Awad, J. A.; Boss, H. J.; Blair, I. A.; Roberts, L. J., II. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 10721.
22. (b) Kayganich-Harrison, K. A.; Rose, D. M.; Murphy, R. C.; Morrow, J. D.; Roberts, L. J., II. J. Lipid Res. 1993, 34, 1229.
23. A small percentage of isoprostane production may be attributed to the action of the COX enzymes. (c) Practicó, D.; Lawson, J. A.; FitzGerald, G. A. J. Biol. Chem. 1995, 270, 9800.
24. (d) Practicó, D.; FitzGerald, G. A. J. Biol. Chem. 1996, 271, 8919.
25. (e) Patrignani, P.; Santini, G.; Panara, M. R.; Sciulli, M.; Greco, A.; Rotondo, M. T.; Giamberardino, M.; Maclouf, J.; Ciabttoni, G.; Patrono, C. Br. J. Pharmacol. 1996, 118, 1285.
26. (a) Patrono, C.; Davi, G.; Falco, A. Chem. Phys. Lipids 2004, 128, 149.
27. For a summary of isoprostane nomenclature, see: (b) Roberts, L. J., II; Taber, D. F.; Morrow, J. D. Prostaglandins 1997, 53, 63.
28. For an alternative nomenclature system, see: (c) Rokach, J.; Khanapure, S. P.; Hwang, S. W.; Adiyaman, M.; Lawson, J. A.; FitzGerald, G. A. Prostaglandins 1997, 54, 853.
29. For a recent synopsis of the pharmacology of isoprostanes and other lipid peroxidation products, see: Chem. Phys. Lipids 2004, 128, 1-193.
30. (a) Randall, M. L.; Tallarico, J. A.; Snapper, M. L. J. Am. Chem. Soc. 1995, 117, 9610.
31. For lead references on ring-opening cross-metathesis applications in total synthesis, see: (b) Grubbs, R. H., Ed.; Handbook of Metathesis; Wiley-VCH: New York, 2003; Vol. 2. Sec. 2.6, and references therein.
32. (a) Schrader, T. O.; Snapper, M. L. Tetrahedron Lett. 2000, 41, 9685.
33. (b) Schrader, T. O.; Snapper, M. L. J. Am. Chem. Soc. 2002, 124, 10998.
34. 2-isoprostanes. see: (a) Taber, D. F.; Kanai, K.; Pina, R. J. Am. Chem. Soc. 1999, 121, 7773.
35. (b) Adiyaman, M.; Lawson, J. A.; Khanapure, S. P.; FitzGerald, G. A.; Rokach, J. Anal. Biochem. 1998, 262, 45.
36. (c) Adiyaman, M.; Lawson, J. A.; FitzGerald, G. A.; Rokach, J. Tetrahedron Lett. 1998, 39, 7039.
37. (d) Durand, T.; Cracowski, J.-L.; Guy, A.; Rossi, J.-C. Bioorg. Med. Chem. Lett. 2001, 11, 2495.
38. (e) Also, see ref 7.
39. For example, see: (a) Marliere, S.; Cracowski, J.-L.; Durband, T.; Chavanon, O.; Bessard, J.; Guy, A.; Stank-Labesque, F.; Ross, J.-C.; Bessard, G. Br. J. Pharmacol. 2002, 135, 1276.
40. (b) Arnaud, C.; Cracowski, J.-L.; Hakim, A.; Durand, T.; Guy, A.; Godin-Ribuot, D.; Bessard, G.; Ribuot, C. Clin. Exp. Pharmacol. Physiol. 2005, 32, 350.
41. (c) Hou, X.; Roberts, L. J.; Gobeil, F., Jr.; Taber, D. F.; Kanai, K.; Abran, D.; Brault, S.; Checchin, D.; Sennlaub, F.; Lachapelle, P.; Varma, D. R.; Chemtob, S. Free Radical Bio. Med. 2004, 36, 163.
42. Choi, T.-L.; Lee, C. W.; Chatterjee, A. K.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 10417.
43. Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168.
44. (a) Fürstner, A.; Radkowski, K.; Wirtz, C.; Goddard, R.; Lehmann, C. W.; Mynott, R. J. Am. Chem. Soc. 2002, 124, 7061.
45. (b) Fürstner, A.; Schlede, M. Adv. Synth. Cat. 2002, 344, 657.
46. (c) Banwell, M. G.; Loong, D. T. J. Org. Biomol. Chem. 2004, 2, 2050.
47. (d) Kaul, R.; Surprenant, S.; Lubell, W. D. J. Org. Chem. 2005, 70, 3838.
48. (e) Davoli, P.; Fava, R.; Morandi, S.; Spaggiari, A.; Prati, F. Tetrahedron 2005, 61, 4427.
49. Milstein, D.; Stille, J. K. J. Org. Chem. 1979, 44, 1613.
50. Yields for these reactions were dependent on the protocol used to separate ruthenium byproducts from the desired material. For optimal results, see: (a) Kim, B. M.; Cho, J. H. Org. Lett. 2003, 5, 531.
51. For early examples of this type of interaction, see: (a) Snapper, M. L.; Tallarico, J. A.; Randall, M. L. J. Am. Chem. Soc. 1997, 119, 1478.
52. (b) Tallarico, J. A.; Bonitatebus, P. J., Jr.; Snapper, M. L. J. Am. Chem. Soc. 1997, 1197157.
53. For a related CM strategy to install a similar sidechain, see: (a) Jacobo, S. H.; Chang, C.-T.; Lee, G.-J.; Lawson, J. A.; Powell, W. S.; Praticó, D.; FitzGerald, G. A.; Rokach, J. J. Org. Chem. 2006, 71, 1370.
54. For a discussion of selective issues in cross-metatheses, see: (b) Chatterjee, A. K.; Choi, T.-L.; Sanders, D. P.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 11360. Catalyst 13 was inefficient in performing the CM either in tandem or separate operations. Conversely, catalyst 15 provided only cyclobutene polymer when subjected to optimal ring-opening under ethylene atmosphere.
55. Corey, E. J.; Helal, C. J. Angew. Chem., Int. Ed. 1998, 37, 1987.
56. Enantiomeric excess determined by HPLC of corresponding ketone. See Supporting Information for details.
57. MacCoss, R. N.; Balskus, E. P.; Ley, S, V. Tetrahedron Lett. 2003, 44, 7779.
58. 1H-NMR analysis of the corresponding secondary alcohol Mosher esters. See Supporting Information for details.
59. The step count doesn't include the recycling steps that were used to enhance the optical purity of these isoprostanes.