Asymmetric synthesis of a prostaglandin D2 receptor antagonist

Journal of Organic Chemistry

Volumn 70, Issue 1, 2005, Pages 268-274

  Campos, Kevin R ^a   Journet, Michel ^a   Lee, Sandra ^a   Grabowski, Edward J J ^a   Tillyer, Richard D ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; HYDROGEN; ISOTOPES; OXIDATION;

ALLERGIC RHINITIS; INDOLINE OXIDATION; RACEMIZATION; STEREOGENIC CENTERS;

SYNTHESIS (CHEMICAL);

2 [(1) CYCLOPENT 2 EN 1 YL] N (2,6 DIBROMO 4 FLUOROPHENYL)ACETAMIDE; ESTER; HYDRAZINE; INDOLE DERIVATIVE; LIGAND; PROSTAGLANDIN D2; PROSTAGLANDIN RECEPTOR BLOCKING AGENT; SULFONE; UNCLASSIFIED DRUG;

ALLERGIC RHINITIS; ALLYLIC REARRANGEMENT; ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL STRUCTURE; CYCLIZATION; DRUG ANALYSIS; DRUG STRUCTURE; HECK REACTION; ISOMERIZATION; OXIDATION; RACEMIZATION;

COMBINATORIAL CHEMISTRY TECHNIQUES; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; INDOLES; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; OXIDATION-REDUCTION; PALLADIUM; RECEPTORS, IMMUNOLOGIC; RECEPTORS, PROSTAGLANDIN; RHINITIS, ALLERGIC, PERENNIAL;

EID: 11844265889     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048305+     Document Type: Article

References (39)

1. Lewis, R, A.; Soter, N. A.; Diamond, P. T.; Austen, K. F.; Oates, J. A.; Roberts, L. J. J. Immunol. 1982, 129, 1627-1631.
2. (a) Matsuoka, T.; Hirata, M.; Tanaka, H.; Takahashi, Y.; Murata, T.; Kabashima, K.; Sugimoto, Y.; Kobayashi, T.; Ushikubi, F.; Aze, Y.; Eguchi, N.; Urade, Y.; Yoshida, N.; Kimura, K.; Mizoguchi, A.; Honda, Y.; Nagai, H.; Narumiya, S.; Kato, M.; Watanabe, M.; Vogler, B.; Awen, B.; Masuda, Y.; Tooyama, Y.; Yoshikoshi, A. Science 2000, 287, 2013-2016.
3. (b) Charlesworth, E. N.; Kagey-Sobotka, A.; Schliemer, R. P.; Norman, P. S.; Lichtenstein, L. M. J. Immunol. 1991, 149, 671-676.
4. (c) Proud, D.; Sweet, J.; Stein, P.; Settipane, R. A.; Kagey-Sobotka, A.; Freidlander, M.; Lichtenstein, L. M. J. Allergy Clin. Immunol. 1990, 85, 896-905.
5. (d) Murray, J. J.; Tonnel, A. B.; Brash, A. R.; Roberts, L. J.; Gosset, P.; Workman, R.; Capron, A.; Oates, J. N. Eng. J. Med. 1986, 315, 800-804.
6. Tsuri, T.; Honma, T.; Hiramatsu, Y.; Mitsumori, S.; Inagaki, M.; Arimura, A.; Yasui, K.; Asanuma, F.; Kishino, J.; Ohtani, M. J. Med. Chem. 1997, 40, 3504-3507.
7. Gribble, G. W. J. Chem. Soc., Perkin Trans. 1 2000, 1045-1075 and references therein.
8. (a) Gribble, G. W. Contemp. Org. Synth. 1994, 1, 1.
9. (b) Hughes, D. L. Org. Prep. Proc. Int. 1993, 25, 607-632.
10. (c) Robinson, B. The Fischer Indole Synthesis; Wiley-Interscience: New York, 1982.
11. (a) Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921-2944.
12. (b) Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1994, 116, 4089-4090.
13. Arunachalam, T.; Fan, H.; Pillai, K. M. R.; Ranganathan, R. S. J. Org. Chem. 1995, 60, 4428-4438.
14. The O-cyclized product 13 was a 2:1 mixture of E/Z imidate isomers.
15. (a) Dounay, A. B.; Overman, L. E. Chem. Rev. 2003, 2945-2964.
16. (b) Link, J. Org. React. 2002, 157.
17. (c) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009-3066.
18. The benefits of Heck conditions performed in aqueous systems have been reported, (a) Zhao, F.; Shirai, M.; Arai, M. J. Mol. Catal. A 2000, 154, 39. (b) Demik, N. N.; Kabachnik, M. M.; Novikova, Z. S.; Beletskaya, I. P. Russ. J. Org. Chem. 1995, 31, 57. (c) Zhang, H. C.; Daves, G. D. Organometallics 1993, 12, 1499. (d) Bumagin, N. A.; More, P. G.; Beletskaya, I. P. J. Organomet. Chem. 1989, 371, 397.
19. The benefits of Heck conditions performed in aqueous systems have been reported, (a) Zhao, F.; Shirai, M.; Arai, M. J. Mol. Catal. A 2000, 154, 39. (b) Demik, N. N.; Kabachnik, M. M.; Novikova, Z. S.; Beletskaya, I. P. Russ. J. Org. Chem. 1995, 31, 57. (c) Zhang, H. C.; Daves, G. D. Organometallics 1993, 12, 1499. (d) Bumagin, N. A.; More, P. G.; Beletskaya, I. P. J. Organomet. Chem. 1989, 371, 397.
20. The benefits of Heck conditions performed in aqueous systems have been reported, (a) Zhao, F.; Shirai, M.; Arai, M. J. Mol. Catal. A 2000, 154, 39. (b) Demik, N. N.; Kabachnik, M. M.; Novikova, Z. S.; Beletskaya, I. P. Russ. J. Org. Chem. 1995, 31, 57. (c) Zhang, H. C.; Daves, G. D. Organometallics 1993, 12, 1499. (d) Bumagin, N. A.; More, P. G.; Beletskaya, I. P. J. Organomet. Chem. 1989, 371, 397.
21. The benefits of Heck conditions performed in aqueous systems have been reported, (a) Zhao, F.; Shirai, M.; Arai, M. J. Mol. Catal. A 2000, 154, 39. (b) Demik, N. N.; Kabachnik, M. M.; Novikova, Z. S.; Beletskaya, I. P. Russ. J. Org. Chem. 1995, 31, 57. (c) Zhang, H. C.; Daves, G. D. Organometallics 1993, 12, 1499. (d) Bumagin, N. A.; More, P. G.; Beletskaya, I. P. J. Organomet. Chem. 1989, 371, 397.
22. (a) Shimada, T.; Nakamura, I.; Yamamoto, Y. J. Am. Chem. Soc. 2004, 10546-10547.
23. (b) Danishefsky, S.; Taniyama, E. Tetrahedron Lett. 1983, 24, 15.
24. For recent examples of tandem Pd-catalyzed processes, see: Pinho, P.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2003, 259-261 and references therein.
25. It is quite possible that Bredt's rule applies to this system which would prohibit olefin isomerization to either "bridgehead" position. Shea, K. J. Tetrahedron 1980, 1683-1715 and references therein.
26. (a) Clive, D. L. J.; Daigneault, S. J. Org. Chem. 1991, 56, 5-5289.
27. (b) Andrieux, J.; Barton, D. H. R.; Patin, H. J. Chem. Soc., Perkin Trans. 1 1977, 359.
28. (c) Grieco, P. A.; Nishizawa, M.; Marinovic, N.; Ehmann, W. J. J. Am. Chem. Soc. 1976, 98, 7102.
29. (a) Baskin, J. M.; Wang, Z. Tetrahedron Lett. 2002, 8479-8483.
30. (b) Suzuki, H.; Abe, H. Tetrahedron Lett. 1995, 36, 6239-6242.
31. (a) Forbes, I. T. Tetrahedron Lett. 1999, 9293-9295.
32. (b) Tietze, L. F.; Buhr, W. Angew. Chem., Int. Ed. Engl. 1995, 1366-1368.
33. (c) Kaufman, M. D.; Greico, P. A. J. Org. Chem. 1994, 59, 7-7198.
34. (d) Simoji, Y.; Saito, F.; Tomita, K.; Morisawa, Y. Heterocycles 1991, 2389-2397.
35. Alternatively, Wilkinson's catalyst was also found to be effective; however hydrogenation with Pd/C was found to produce isomerization products with some degradation of enantiomeric excess.
36. No reaction was observed when 20 was treated with DDQ. Lee, S.; Lim, H.-J.; Cha, K.; Sulikowski, G. A. Tetrahedron 1997, 53, 16521-16532.
37. Treatment with NBS afforded decomposition, which was the result of overoxidation of 20. Ko, C.-W.; Chou, T. J. Org. Chem. 1998, 63, 4645-4653.
38. No oxidation was observed using Pd/C in a variety of solvents. Pelcman, B., Gribble, G. W. Tetrahedron Lett. 1990, 31, 2381-2384.
39. No oxidation was observed. Inada, A.; Nakamura, Y.; Morita, Y. Chem. Lett. 1980, 12.