Preparation of isoprostanes and neuroprostanes

Journal of the American Chemical Society

Volumn 124, Issue 42, 2002, Pages 12424-12425

  Quan, Long Guo ^a   Cha, Jin Kun ^a,b  

^a UNIVERSITY OF ALABAMA   (United States)

^b WAYNE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

12 EPIPROSTAGLANDIN F2 ALPHA; CYCLOPENTANE DERIVATIVE; ISOPROSTANE; NEUROPROSTANE; PROSTAGLANDIN DERIVATIVE; PROSTAGLANDIN F2 ALPHA DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; STEREOCHEMISTRY; SYNTHESIS;

DINOPROST; DOCOSAHEXAENOIC ACIDS; ISOPROSTANES; STEREOISOMERISM;

EID: 0037164005     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja027451z     Document Type: Article

References (34)

1. For representative reviews, see: (a) Collins, P. W.; Djuric, S. W. Chem. Rev. 1993, 93, 1533. (b) Roberts, S. M.; Santoro, M. G.; Sickle, E. S. J. Chem. Soc., Perkin Trans. 1 2002, 1735. (c) For a compilation of recent synthetic approaches, see: Taber, D. F.; Teng, D. J. Org. Chem. 2002, 67, 1607 and references therein.
2. For representative reviews, see: (a) Collins, P. W.; Djuric, S. W. Chem. Rev. 1993, 93, 1533. (b) Roberts, S. M.; Santoro, M. G.; Sickle, E. S. J. Chem. Soc., Perkin Trans. 1 2002, 1735. (c) For a compilation of recent synthetic approaches, see: Taber, D. F.; Teng, D. J. Org. Chem. 2002, 67, 1607 and references therein.
3. For representative reviews, see: (a) Collins, P. W.; Djuric, S. W. Chem. Rev. 1993, 93, 1533. (b) Roberts, S. M.; Santoro, M. G.; Sickle, E. S. J. Chem. Soc., Perkin Trans. 1 2002, 1735. (c) For a compilation of recent synthetic approaches, see: Taber, D. F.; Teng, D. J. Org. Chem. 2002, 67, 1607 and references therein.
4. (a) 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.
5. (b) Roberts, L. J., II; Montine, T. J.; Markesbery, W. R.; Tapper, A. R.; Hardy, P.; Chemtob, S.; Dettbarn, W. D.; Morrow, J. D. J. Biol. Chem. 1998, 273, 13605.
6. (c) Praticò, D.; Barry, O. P.; Lawson, J. A.; Adiyaman, M.; Hwang, S.-W.; Khanapure, S. P.; Iuliano, L.; Rokach, J.; FitzGerald, G. A. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 3449.
7. For recent work on an isolevuglandin hypothesis, see: Subbanagounder, G.; Salomon, R. G.; Murthi, K. K.; Brame, C.; Roberts, L. J., II. J. Org. Chem. 1997, 62, 7658.
8. Four previous syntheses of 1 and other isoprostanes: (a) Larock, R. C.; Lee, N. H. J. Am. Chem. Soc. 1991, 113, 7815. (b) Vionnet, J.-P.; Renaud, P. Helv. Chim. Acta 1994, 77, 1781. (c) Mulzer, J.; Kermanchahi, A. K.; Buschmann, J.; Luger, P. Liebigs Ann. Chem. 1994, 531. (d) Hwang, S.-W.; Adiyaman, M.; Khanapure, S.; Schio, L.; Rokach, J. J. Am. Chem. Soc. 1994, 116, 10829. (e) Hwang, S.-W.; Adiyaman, M.; Khanapure, S. P.; Rokach, J. Tetrahedron Lett. 1996, 37, 779. (f) Roland, A.; Durand, T.; Rondot, B.; Vidal, J.-P.; Rossi, J.-C. Bull. Soc. Chim. Fr. 1996, 133, 1149. (g) Taber, D. F.; Herr, R. J.; Gleave, D. M. J. Org. Chem. 1997, 62, 194. (h) Durand, T.; Guy, A.; Vidal, J.-P.; Rossi, J.-C. J. Org. Chem. 2002, 67, 3615. (i) Schrader, T. O.; Snapper, M. C. J. Am. Chem. Soc. 2002, 124, ASAP.
9. Four previous syntheses of 1 and other isoprostanes: (a) Larock, R. C.; Lee, N. H. J. Am. Chem. Soc. 1991, 113, 7815. (b) Vionnet, J.-P.; Renaud, P. Helv. Chim. Acta 1994, 77, 1781. (c) Mulzer, J.; Kermanchahi, A. K.; Buschmann, J.; Luger, P. Liebigs Ann. Chem. 1994, 531. (d) Hwang, S.-W.; Adiyaman, M.; Khanapure, S.; Schio, L.; Rokach, J. J. Am. Chem. Soc. 1994, 116, 10829. (e) Hwang, S.-W.; Adiyaman, M.; Khanapure, S. P.; Rokach, J. Tetrahedron Lett. 1996, 37, 779. (f) Roland, A.; Durand, T.; Rondot, B.; Vidal, J.-P.; Rossi, J.-C. Bull. Soc. Chim. Fr. 1996, 133, 1149. (g) Taber, D. F.; Herr, R. J.; Gleave, D. M. J. Org. Chem. 1997, 62, 194. (h) Durand, T.; Guy, A.; Vidal, J.-P.; Rossi, J.-C. J. Org. Chem. 2002, 67, 3615. (i) Schrader, T. O.; Snapper, M. C. J. Am. Chem. Soc. 2002, 124, ASAP.
10. Four previous syntheses of 1 and other isoprostanes: (a) Larock, R. C.; Lee, N. H. J. Am. Chem. Soc. 1991, 113, 7815. (b) Vionnet, J.-P.; Renaud, P. Helv. Chim. Acta 1994, 77, 1781. (c) Mulzer, J.; Kermanchahi, A. K.; Buschmann, J.; Luger, P. Liebigs Ann. Chem. 1994, 531. (d) Hwang, S.-W.; Adiyaman, M.; Khanapure, S.; Schio, L.; Rokach, J. J. Am. Chem. Soc. 1994, 116, 10829. (e) Hwang, S.-W.; Adiyaman, M.; Khanapure, S. P.; Rokach, J. Tetrahedron Lett. 1996, 37, 779. (f) Roland, A.; Durand, T.; Rondot, B.; Vidal, J.-P.; Rossi, J.-C. Bull. Soc. Chim. Fr. 1996, 133, 1149. (g) Taber, D. F.; Herr, R. J.; Gleave, D. M. J. Org. Chem. 1997, 62, 194. (h) Durand, T.; Guy, A.; Vidal, J.-P.; Rossi, J.-C. J. Org. Chem. 2002, 67, 3615. (i) Schrader, T. O.; Snapper, M. C. J. Am. Chem. Soc. 2002, 124, ASAP.
11. Four previous syntheses of 1 and other isoprostanes: (a) Larock, R. C.; Lee, N. H. J. Am. Chem. Soc. 1991, 113, 7815. (b) Vionnet, J.-P.; Renaud, P. Helv. Chim. Acta 1994, 77, 1781. (c) Mulzer, J.; Kermanchahi, A. K.; Buschmann, J.; Luger, P. Liebigs Ann. Chem. 1994, 531. (d) Hwang, S.-W.; Adiyaman, M.; Khanapure, S.; Schio, L.; Rokach, J. J. Am. Chem. Soc. 1994, 116, 10829. (e) Hwang, S.-W.; Adiyaman, M.; Khanapure, S. P.; Rokach, J. Tetrahedron Lett. 1996, 37, 779. (f) Roland, A.; Durand, T.; Rondot, B.; Vidal, J.-P.; Rossi, J.-C. Bull. Soc. Chim. Fr. 1996, 133, 1149. (g) Taber, D. F.; Herr, R. J.; Gleave, D. M. J. Org. Chem. 1997, 62, 194. (h) Durand, T.; Guy, A.; Vidal, J.-P.; Rossi, J.-C. J. Org. Chem. 2002, 67, 3615. (i) Schrader, T. O.; Snapper, M. C. J. Am. Chem. Soc. 2002, 124, ASAP.
12. Four previous syntheses of 1 and other isoprostanes: (a) Larock, R. C.; Lee, N. H. J. Am. Chem. Soc. 1991, 113, 7815. (b) Vionnet, J.-P.; Renaud, P. Helv. Chim. Acta 1994, 77, 1781. (c) Mulzer, J.; Kermanchahi, A. K.; Buschmann, J.; Luger, P. Liebigs Ann. Chem. 1994, 531. (d) Hwang, S.-W.; Adiyaman, M.; Khanapure, S.; Schio, L.; Rokach, J. J. Am. Chem. Soc. 1994, 116, 10829. (e) Hwang, S.-W.; Adiyaman, M.; Khanapure, S. P.; Rokach, J. Tetrahedron Lett. 1996, 37, 779. (f) Roland, A.; Durand, T.; Rondot, B.; Vidal, J.-P.; Rossi, J.-C. Bull. Soc. Chim. Fr. 1996, 133, 1149. (g) Taber, D. F.; Herr, R. J.; Gleave, D. M. J. Org. Chem. 1997, 62, 194. (h) Durand, T.; Guy, A.; Vidal, J.-P.; Rossi, J.-C. J. Org. Chem. 2002, 67, 3615. (i) Schrader, T. O.; Snapper, M. C. J. Am. Chem. Soc. 2002, 124, ASAP.
13. Four previous syntheses of 1 and other isoprostanes: (a) Larock, R. C.; Lee, N. H. J. Am. Chem. Soc. 1991, 113, 7815. (b) Vionnet, J.-P.; Renaud, P. Helv. Chim. Acta 1994, 77, 1781. (c) Mulzer, J.; Kermanchahi, A. K.; Buschmann, J.; Luger, P. Liebigs Ann. Chem. 1994, 531. (d) Hwang, S.-W.; Adiyaman, M.; Khanapure, S.; Schio, L.; Rokach, J. J. Am. Chem. Soc. 1994, 116, 10829. (e) Hwang, S.-W.; Adiyaman, M.; Khanapure, S. P.; Rokach, J. Tetrahedron Lett. 1996, 37, 779. (f) Roland, A.; Durand, T.; Rondot, B.; Vidal, J.-P.; Rossi, J.-C. Bull. Soc. Chim. Fr. 1996, 133, 1149. (g) Taber, D. F.; Herr, R. J.; Gleave, D. M. J. Org. Chem. 1997, 62, 194. (h) Durand, T.; Guy, A.; Vidal, J.-P.; Rossi, J.-C. J. Org. Chem. 2002, 67, 3615. (i) Schrader, T. O.; Snapper, M. C. J. Am. Chem. Soc. 2002, 124, ASAP.
14. Four previous syntheses of 1 and other isoprostanes: (a) Larock, R. C.; Lee, N. H. J. Am. Chem. Soc. 1991, 113, 7815. (b) Vionnet, J.-P.; Renaud, P. Helv. Chim. Acta 1994, 77, 1781. (c) Mulzer, J.; Kermanchahi, A. K.; Buschmann, J.; Luger, P. Liebigs Ann. Chem. 1994, 531. (d) Hwang, S.-W.; Adiyaman, M.; Khanapure, S.; Schio, L.; Rokach, J. J. Am. Chem. Soc. 1994, 116, 10829. (e) Hwang, S.-W.; Adiyaman, M.; Khanapure, S. P.; Rokach, J. Tetrahedron Lett. 1996, 37, 779. (f) Roland, A.; Durand, T.; Rondot, B.; Vidal, J.-P.; Rossi, J.-C. Bull. Soc. Chim. Fr. 1996, 133, 1149. (g) Taber, D. F.; Herr, R. J.; Gleave, D. M. J. Org. Chem. 1997, 62, 194. (h) Durand, T.; Guy, A.; Vidal, J.-P.; Rossi, J.-C. J. Org. Chem. 2002, 67, 3615. (i) Schrader, T. O.; Snapper, M. C. J. Am. Chem. Soc. 2002, 124, ASAP.
15. Four previous syntheses of 1 and other isoprostanes: (a) Larock, R. C.; Lee, N. H. J. Am. Chem. Soc. 1991, 113, 7815. (b) Vionnet, J.-P.; Renaud, P. Helv. Chim. Acta 1994, 77, 1781. (c) Mulzer, J.; Kermanchahi, A. K.; Buschmann, J.; Luger, P. Liebigs Ann. Chem. 1994, 531. (d) Hwang, S.-W.; Adiyaman, M.; Khanapure, S.; Schio, L.; Rokach, J. J. Am. Chem. Soc. 1994, 116, 10829. (e) Hwang, S.-W.; Adiyaman, M.; Khanapure, S. P.; Rokach, J. Tetrahedron Lett. 1996, 37, 779. (f) Roland, A.; Durand, T.; Rondot, B.; Vidal, J.-P.; Rossi, J.-C. Bull. Soc. Chim. Fr. 1996, 133, 1149. (g) Taber, D. F.; Herr, R. J.; Gleave, D. M. J. Org. Chem. 1997, 62, 194. (h) Durand, T.; Guy, A.; Vidal, J.-P.; Rossi, J.-C. J. Org. Chem. 2002, 67, 3615. (i) Schrader, T. O.; Snapper, M. C. J. Am. Chem. Soc. 2002, 124, ASAP.
16. Lai, S.; Lee, D.; U, J. S.; Cha, J. K. J. Org. Chem. 1999, 64, 7213.
17. For recent reviews on the Stille reaction, see: (a) Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. 1997, 50, 1. (b) Mitchell, T. N. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; Chapter 4.
18. For recent reviews on the Stille reaction, see: (a) Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. 1997, 50, 1. (b) Mitchell, T. N. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; Chapter 4.
19. For recent reviews on cross coupling of organosilicon reagents, see: (a) Hiyama, T. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; Chapter 10. (b) Hatanaka, Y.; Hiyama, T. Synlett 1991, 845.
20. For recent reviews on cross coupling of organosilicon reagents, see: (a) Hiyama, T. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; Chapter 10. (b) Hatanaka, Y.; Hiyama, T. Synlett 1991, 845.
21. (a) Stork, G.; Suh, H. S.; Kim, G. J. Am. Chem. Soc. 1991, 113, 7054. (b) Stork, G.; La Clair, J. J. J. Am. Chem. Soc. 1996, 118, 247. (c) Shuto, S.; Sugimoto, I.; Abe, H.; Matsuda, A. J. Am. Chem. Soc. 2000, 122, 1343. For recent reviews on the use of silicon-tethers, see; (d) Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253. (e) Fensterbank, L.; Malacria, M.; Sieburth, S. McN. Synthesis 1997, 813. (f) Gauther, D. R., Jr.; Zandi, K. S.; Shea, K. J. Tetrahedron 1998, 54, 2289.
22. (a) Stork, G.; Suh, H. S.; Kim, G. J. Am. Chem. Soc. 1991, 113, 7054. (b) Stork, G.; La Clair, J. J. J. Am. Chem. Soc. 1996, 118, 247. (c) Shuto, S.; Sugimoto, I.; Abe, H.; Matsuda, A. J. Am. Chem. Soc. 2000, 122, 1343. For recent reviews on the use of silicon-tethers, see; (d) Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253. (e) Fensterbank, L.; Malacria, M.; Sieburth, S. McN. Synthesis 1997, 813. (f) Gauther, D. R., Jr.; Zandi, K. S.; Shea, K. J. Tetrahedron 1998, 54, 2289.
23. (a) Stork, G.; Suh, H. S.; Kim, G. J. Am. Chem. Soc. 1991, 113, 7054. (b) Stork, G.; La Clair, J. J. J. Am. Chem. Soc. 1996, 118, 247. (c) Shuto, S.; Sugimoto, I.; Abe, H.; Matsuda, A. J. Am. Chem. Soc. 2000, 122, 1343. For recent reviews on the use of silicon-tethers, see; (d) Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253. (e) Fensterbank, L.; Malacria, M.; Sieburth, S. McN. Synthesis 1997, 813. (f) Gauther, D. R., Jr.; Zandi, K. S.; Shea, K. J. Tetrahedron 1998, 54, 2289.
24. (a) Stork, G.; Suh, H. S.; Kim, G. J. Am. Chem. Soc. 1991, 113, 7054. (b) Stork, G.; La Clair, J. J. J. Am. Chem. Soc. 1996, 118, 247. (c) Shuto, S.; Sugimoto, I.; Abe, H.; Matsuda, A. J. Am. Chem. Soc. 2000, 122, 1343. For recent reviews on the use of silicon-tethers, see; (d) Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253. (e) Fensterbank, L.; Malacria, M.; Sieburth, S. McN. Synthesis 1997, 813. (f) Gauther, D. R., Jr.; Zandi, K. S.; Shea, K. J. Tetrahedron 1998, 54, 2289.
25. (a) Stork, G.; Suh, H. S.; Kim, G. J. Am. Chem. Soc. 1991, 113, 7054. (b) Stork, G.; La Clair, J. J. J. Am. Chem. Soc. 1996, 118, 247. (c) Shuto, S.; Sugimoto, I.; Abe, H.; Matsuda, A. J. Am. Chem. Soc. 2000, 122, 1343. For recent reviews on the use of silicon-tethers, see; (d) Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253. (e) Fensterbank, L.; Malacria, M.; Sieburth, S. McN. Synthesis 1997, 813. (f) Gauther, D. R., Jr.; Zandi, K. S.; Shea, K. J. Tetrahedron 1998, 54, 2289.
26. (a) Stork, G.; Suh, H. S.; Kim, G. J. Am. Chem. Soc. 1991, 113, 7054. (b) Stork, G.; La Clair, J. J. J. Am. Chem. Soc. 1996, 118, 247. (c) Shuto, S.; Sugimoto, I.; Abe, H.; Matsuda, A. J. Am. Chem. Soc. 2000, 122, 1343. For recent reviews on the use of silicon-tethers, see; (d) Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253. (e) Fensterbank, L.; Malacria, M.; Sieburth, S. McN. Synthesis 1997, 813. (f) Gauther, D. R., Jr.; Zandi, K. S.; Shea, K. J. Tetrahedron 1998, 54, 2289.
27. While this work was in progress, Denmark disclosed the first example of intramolecular silicon-assisted cross-coupling reactions of functionalized siloxanes and alkenyl iodides: Denmark, S. E.; Yang, S.-M. J. Am. Chem. Soc. 2002, 124, 2102.
28. (a) Fugami, K.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1987, 28, 809.
29. (b) Chemler, S. R.; Trauner, D.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2001, 40, 4544.
30. 2 group. In the present example, the tandem Heck-Heck sequence was believed to be unfavorable due to high congestion and strain associated with the corresponding cagelike tricyclic intermediate.
31. (b) Tsuji, J. Palladium Reagents and Catalysts; Wiley: New York, 1995; pp 135-136.
32. (c) Widenhoefer, R. A.; DeCarli, M. A. J. Am. Chem. Soc. 1998, 120, 3805.
33. (d) Cf. Knochel, P. Synlett 1995, 393.