Diastereoselective Synthesis of an Isoprostane: (±)-8-epi-PGF2α Ethyl Ester

Journal of Organic Chemistry

Volumn 62, Issue 1, 1997, Pages 194-198

  Taber, Douglass F ^a   Herr, R Jason ^a   Gleave, D Mark ^a  

^a UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PROSTAGLANDIN DERIVATIVE; PROSTAGLANDIN F2 ALPHA ETHYL ESTER; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031030953     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9616365     Document Type: Article

References (32)

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2. (b) 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.
3. Morrow, J. D.; Awad, J. A.; Boss, H. J.; Blair, I. A.; Roberts, L. J., II. Proc. Nat. Acad. Sci. U.S.A. 1992, 89, 10721.
4. Initial reports on isoprostane isolation and studies include: (a) Morrow, J. D.; Minton, T. A.; Roberts, L. J., II. Prostaglandins 1992, 44, 155. (b) Fukunaga, M.; Makita, N.; Roberts, L. J., II; Morrow, J. D.; Takahashi, K.; Badr, K. F. Am. J. Physiol. (Cell Physiol 33) 1993, 264, C1619. (c) 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. (d) Morrow, J. D.; Awad, J. A.; Kato, T.; Takahashi, K.; Badr, K. F.; Roberts, L. J., II; Burk, R. F. J. Clin. Invest. 1992, 90, 2502. (e) Morrow, J. D.; Badr, K. F.; Roberts, L. J., II. Biochim. Biophys. Acta 1994, 1210, 244. Also see: Parsons, W. G. I.; Roberts, L. J., II. In Advances in Prostaglandin, Thromboxane, and Leukotriene Research Samuelsson, B., Wong, P. Y. K., Sun, F. F., Eds.; Raven Press: New York, 1988; Vol. 19, p 499.
5. Initial reports on isoprostane isolation and studies include: (a) Morrow, J. D.; Minton, T. A.; Roberts, L. J., II. Prostaglandins 1992, 44, 155. (b) Fukunaga, M.; Makita, N.; Roberts, L. J., II; Morrow, J. D.; Takahashi, K.; Badr, K. F. Am. J. Physiol. (Cell Physiol 33) 1993, 264, C1619. (c) 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. (d) Morrow, J. D.; Awad, J. A.; Kato, T.; Takahashi, K.; Badr, K. F.; Roberts, L. J., II; Burk, R. F. J. Clin. Invest. 1992, 90, 2502. (e) Morrow, J. D.; Badr, K. F.; Roberts, L. J., II. Biochim. Biophys. Acta 1994, 1210, 244. Also see: Parsons, W. G. I.; Roberts, L. J., II. In Advances in Prostaglandin, Thromboxane, and Leukotriene Research Samuelsson, B., Wong, P. Y. K., Sun, F. F., Eds.; Raven Press: New York, 1988; Vol. 19, p 499.
6. Initial reports on isoprostane isolation and studies include: (a) Morrow, J. D.; Minton, T. A.; Roberts, L. J., II. Prostaglandins 1992, 44, 155. (b) Fukunaga, M.; Makita, N.; Roberts, L. J., II; Morrow, J. D.; Takahashi, K.; Badr, K. F. Am. J. Physiol. (Cell Physiol 33) 1993, 264, C1619. (c) 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. (d) Morrow, J. D.; Awad, J. A.; Kato, T.; Takahashi, K.; Badr, K. F.; Roberts, L. J., II; Burk, R. F. J. Clin. Invest. 1992, 90, 2502. (e) Morrow, J. D.; Badr, K. F.; Roberts, L. J., II. Biochim. Biophys. Acta 1994, 1210, 244. Also see: Parsons, W. G. I.; Roberts, L. J., II. In Advances in Prostaglandin, Thromboxane, and Leukotriene Research Samuelsson, B., Wong, P. Y. K., Sun, F. F., Eds.; Raven Press: New York, 1988; Vol. 19, p 499.
7. Initial reports on isoprostane isolation and studies include: (a) Morrow, J. D.; Minton, T. A.; Roberts, L. J., II. Prostaglandins 1992, 44, 155. (b) Fukunaga, M.; Makita, N.; Roberts, L. J., II; Morrow, J. D.; Takahashi, K.; Badr, K. F. Am. J. Physiol. (Cell Physiol 33) 1993, 264, C1619. (c) 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. (d) Morrow, J. D.; Awad, J. A.; Kato, T.; Takahashi, K.; Badr, K. F.; Roberts, L. J., II; Burk, R. F. J. Clin. Invest. 1992, 90, 2502. (e) Morrow, J. D.; Badr, K. F.; Roberts, L. J., II. Biochim. Biophys. Acta 1994, 1210, 244. Also see: Parsons, W. G. I.; Roberts, L. J., II. In Advances in Prostaglandin, Thromboxane, and Leukotriene Research Samuelsson, B., Wong, P. Y. K., Sun, F. F., Eds.; Raven Press: New York, 1988; Vol. 19, p 499.
8. Initial reports on isoprostane isolation and studies include: (a) Morrow, J. D.; Minton, T. A.; Roberts, L. J., II. Prostaglandins 1992, 44, 155. (b) Fukunaga, M.; Makita, N.; Roberts, L. J., II; Morrow, J. D.; Takahashi, K.; Badr, K. F. Am. J. Physiol. (Cell Physiol 33) 1993, 264, C1619. (c) 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. (d) Morrow, J. D.; Awad, J. A.; Kato, T.; Takahashi, K.; Badr, K. F.; Roberts, L. J., II; Burk, R. F. J. Clin. Invest. 1992, 90, 2502. (e) Morrow, J. D.; Badr, K. F.; Roberts, L. J., II. Biochim. Biophys. Acta 1994, 1210, 244. Also see: Parsons, W. G. I.; Roberts, L. J., II. In Advances in Prostaglandin, Thromboxane, and Leukotriene Research Samuelsson, B., Wong, P. Y. K., Sun, F. F., Eds.; Raven Press: New York, 1988; Vol. 19, p 499.
9. Initial reports on isoprostane isolation and studies include: (a) Morrow, J. D.; Minton, T. A.; Roberts, L. J., II. Prostaglandins 1992, 44, 155. (b) Fukunaga, M.; Makita, N.; Roberts, L. J., II; Morrow, J. D.; Takahashi, K.; Badr, K. F. Am. J. Physiol. (Cell Physiol 33) 1993, 264, C1619. (c) 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. (d) Morrow, J. D.; Awad, J. A.; Kato, T.; Takahashi, K.; Badr, K. F.; Roberts, L. J., II; Burk, R. F. J. Clin. Invest. 1992, 90, 2502. (e) Morrow, J. D.; Badr, K. F.; Roberts, L. J., II. Biochim. Biophys. Acta 1994, 1210, 244. Also see: Parsons, W. G. I.; Roberts, L. J., II. In Advances in Prostaglandin, Thromboxane, and Leukotriene Research Samuelsson, B., Wong, P. Y. K., Sun, F. F., Eds.; Raven Press: New York, 1988; Vol. 19, p 499.
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13. (a) Longmire, A. W.; Roberts, L. J., II; Morrow, J. D. Prostaglandins 1994, 48, 247.
14. (b) Fukunaga, M.; Takahashi, K.; Badr, K. F. Biochem. Biophys. Res. Commun. 1993, 195, 507.
15. 2α (2) has been reported: Hwang, S. W.; Adiyaman, M.; Khanapure, S.; Schio, L.; Rokach, J. J. Am. Chem. Soc. 1994, 116, 10829. Three syntheses of the 12-epi isomer have been reported: (b) Larock, R. C.; Lee, N. H. J. Am. Chem. Soc. 1991, 113, 7815. (c) Vionnet, J.-P.; Renaud, P. Helv. Chim. Acta 1994, 77, 1781. (d) Hwang, S. W.; Adiyaman, M.; Khanapure, S. P.; Rokach, J. Tetrahedron Lett. 1996, 37, 779.
16. 2α (2) has been reported: Hwang, S. W.; Adiyaman, M.; Khanapure, S.; Schio, L.; Rokach, J. J. Am. Chem. Soc. 1994, 116, 10829. Three syntheses of the 12-epi isomer have been reported: (b) Larock, R. C.; Lee, N. H. J. Am. Chem. Soc. 1991, 113, 7815. (c) Vionnet, J.-P.; Renaud, P. Helv. Chim. Acta 1994, 77, 1781. (d) Hwang, S. W.; Adiyaman, M.; Khanapure, S. P.; Rokach, J. Tetrahedron Lett. 1996, 37, 779.
17. 2α (2) has been reported: Hwang, S. W.; Adiyaman, M.; Khanapure, S.; Schio, L.; Rokach, J. J. Am. Chem. Soc. 1994, 116, 10829. Three syntheses of the 12-epi isomer have been reported: (b) Larock, R. C.; Lee, N. H. J. Am. Chem. Soc. 1991, 113, 7815. (c) Vionnet, J.-P.; Renaud, P. Helv. Chim. Acta 1994, 77, 1781. (d) Hwang, S. W.; Adiyaman, M.; Khanapure, S. P.; Rokach, J. Tetrahedron Lett. 1996, 37, 779.
18. 2α (2) has been reported: Hwang, S. W.; Adiyaman, M.; Khanapure, S.; Schio, L.; Rokach, J. J. Am. Chem. Soc. 1994, 116, 10829. Three syntheses of the 12-epi isomer have been reported: (b) Larock, R. C.; Lee, N. H. J. Am. Chem. Soc. 1991, 113, 7815. (c) Vionnet, J.-P.; Renaud, P. Helv. Chim. Acta 1994, 77, 1781. (d) Hwang, S. W.; Adiyaman, M.; Khanapure, S. P.; Rokach, J. Tetrahedron Lett. 1996, 37, 779.
19. (e) A total synthesis of a "type I" isoprostane 3 has also recently been reported: Adiyaman, M.; Lawson, J. A.; Hwang, S.-W.; Kanapure, S. P.; FitzGerald, G. A.; Rokach, J. Tetrahedron Lett. 1996, 37, 4849.
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24. Bhamidipati, R., unpublished results, University of Delaware.
25. This low yield was due to complications involving the acidic protons α to the ester functionality. When precursor i was used, the two-step process yields diazo ketone ii in 60% yield (eq 1). Chemical Equation Presented it.
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32. For a summary of general experimental procedures, see: Taber, D. F.; Houze, J. B. J. Org. Chem. 1994, 59, 4004.