Enantio- and stereospecific syntheses of 15(R)-Me-PGD2, a potent and selective DP2-receptor agonist

Journal of Organic Chemistry

Volumn 73, Issue 18, 2008, Pages 7213-7218

  Patel, Pranav ^a   Lee, Gue Jae ^a   Kim, Seongjin ^a   Grant, Gail E ^b   Powell, William S ^b   Rokach, Joshua ^a  

^a Florida Institute of Technology ^*  (United States)

^b MCGILL UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL REACTIONS;

CHEMICAL EQUATIONS; ENANTIO; TOTAL SYNTHESIS;

SYNTHESIS (CHEMICAL);

ALKENE; PROSTAGLANDIN D2; PROSTAGLANDIN DERIVATIVE; PROSTAGLANDIN RECEPTOR STIMULATING AGENT; PROSTANOID;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CROSS REACTION; ENANTIOSELECTIVITY; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOSPECIFICITY; SYNTHESIS;

ANIMALS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; MOLECULAR CONFORMATION; PROSTAGLANDIN D2; RATS; RECEPTORS, IMMUNOLOGIC; RECEPTORS, PROSTAGLANDIN; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; TIME FACTORS;

EID: 52449099578     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo801190m     Document Type: Article

References (29)

1. Monneret, G.; Gravel, S.; Diamond, M.; Rokach, J.; Powell, W. S. Blood 2001, 98, 1942.
2. Hirai, H.; Tanaka, K.; Takano, S.; Ichimasa, M.; Nakamura, M.; Nagata, K. J. Immunol. 2002, 168, 981.
3. Monneret, G.; Cossette, C.; Gravel, S.; Rokach, J.; Powell, W. S. J. Pharmacol. Exp. Ther. 2003, 304, 349.
4. Kim, S.; Bellone, S.; Maxey, K.; Powell, W. S.; Lee, G. J.; Rokach, J. Bioorg. Med. Chem. Lett. 2005, 15, 1873.
5. Cossette, C.; Walsh, S. E.; Kim, S.; Lee, G. J.; Lawson, J. A.; Bellone, S.; Rokach, J.; Powell, W. S. J. Pharmacol. Exp. Ther. 2007, 320, 173.
6. Leblanc, Y.; Fitzsimmons, B. J.; Adams, J.; Rokach, J. Tetrahedron Lett. 1985, 26, 1399.
7. Cram, D. J.; Elhafez, F. A. A. J. Am. Chem. Soc. 1952, 74, 5828.
8. Cherest, M.; Felkin, H.; Prudent, N. Tetrahedron Lett. 1968, 2199.
9. Reetz, M. T.; Jung, A. J. Am. Chem. Soc. 1983, 105, 4833.
10. Evans, D. A.; Allison, B. D.; Yang, M. G. Tetrahedron Lett. 1999, 40, 4457.
11. Rokach, J. Leukotrienes and Lipoxygenases, Chemical, Biological and Clinical Aspects, 1st ed.; Elsevier Science: Amsterdam, The Netherlands, 1989; Vol. 11.
12. Kutner, A.; Chodynski, M.; Halkes, S. J. Synth. Commun. 1996, 26, 1175.
13. Rodriguez, A.; Nomen, M.; Spur, B. W.; Godfroid, J. J. Tetrahedron Lett. 1999, 40, 5161.
14. Jacobo, S. H.; Chang, C. T.; Lee, G. J.; Lawson, J. A.; Powell, W. S.; Pratico, D.; Fitzgerald, G. A.; Rokach, J. J. Org. Chem. 2006, 71, 1370.
15. Noyori, R.; Tomino, I.; Yamada, M.; Nishizawa, M. J. Am. Chem. Soc. 1984106, 6717.
16. Julia, M.; Paris, J. M. Tetrahedron Lett. 1973, 14, 4833.
17. Noyori, R.; Tomino, I.; Tanimoto, Y.; Nishizawa, M. J. Am. Chem. Soc. 1984, 106, 6709.
18. For other methods, see: (a) Taber, D. F.; Xu, M.; Hartnett, J. C. J. Am. Chem. Soc. 2002, 124, 13121.
19. (b) Larock, R. C.; Lee, N. H. J. Am. Chem. Soc. 1991, 113, 7815.
20. (c) Quan, L. G.; Cha, J. K. J. Am. Chem. Soc. 2002, 124, 12424.
21. (a) Schrader, T. O.; Snapper, M. L. Tetrahedron Lett. 2000, 41, 9685.
22. (b) Schrader, T. O.; Snapper, M. L. J. Am. Chem. Soc. 2002, 124, 10998.
23. (a) Shizuka, M.; Snapper, M. L. Synthesis 2007, 15, 2397.
24. (b) Pandya, B. A.; Snapper, M. L. J. Chromatogr. B 2008, 73, 3754.
25. (c) Sheddan, N. A.; Mulzer, J. Org. Lett. 2006, 8, 3101.
26. (d) Sheddan, N.; Arion, V. B.; Mulzer, J. Tetrahedron Lett. 2006, 47, 6689.
27. After this work was completed, an interesting related application in the synthesis of pladienolides B and D was brought to our attention by one of the reviewers: Kanada, R. M.; Itoh, D.; Nagai, M.; Niijima, J.; Asai, N.; Mizui, Y.; Abe, S.; Kotake, Y. Angew. Chem., Int. Ed. 2007, 46, 4350.
28. Bundy, G. L.; Morton, D. R.; Peterson, D. C.; Nishizawa, E. E.; Miller, W. L. J. Med. Chem. 1983, 26, 790.
29. Almishri, W.; Cossette, C.; Rokach, J.; Martin, J. G.; Hamid, Q.; Powell, W. S. J. Pharmacol. Exp. Ther. 2005, 313, 64.