Synthesis of prostaglandin E2 methyl ester on a soluble-polymer support for the construction of prostanoid libraries

Journal of the American Chemical Society

Volumn 119, Issue 37, 1997, Pages 8724-8725

  Chen, Shaoqing ^a   Janda, Kim D ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

POLYMER; PROSTAGLANDIN E2 METHYL ESTER;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 0030883333     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja971634h     Document Type: Article

References (45)

1. Samuelsson, B.; Paoletti, R. Advances in Prostaglandin, Thromboxane, and Leukotriene Research; Raven: New York, 1983-1989; Vols. 11 19.
2. Collins, P. W.; Djuric, S. W. Chem. Reu. 1993, 93, 1533.
3. Reviews: (a) Chaiken, I. M.; Janda, K. D. Molecular Diversity and Combinatorial Chemistry: Libraries and Drug Discovery; Chaiken, I. M., Janda, K. D., Eds.; American Chemistry Society: Washington, DC, 1995.
4. (b) Balkenhohl, F.; von dem Bussche-Hunnefeld, C.; Lansky, A.; Zechel, C. Angen: Chem., Int. Ed. Engl. 1996, 35, 2288.
5. Terrett, N. K.; Gardner, M.; Gordon, D. W.; Kobylecki, R. J.; Steel, J. Tetrahedron 1995, 57, 8135.
6. Liskamp, R. M. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 633.
7. (e) Gallop, M. A.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gordon, E. M. J. Med. Chem. 1994, 37, 1233.
8. (f) Gordon, E. M.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gallop, M. A. J. Med. Chem. 1994, 37, 1385.
9. (a) Thompson, L. A.; Ellman, J. A. Chem. Reu. 1996, 96, 555.
10. (b) Ellman, J. A. Ace. Chem. Res. 1996, 29, 132.
11. Armstrong, R. W.; Combs, A. P.; Tempest, P. A.; Brown, S. D.; Keating, T. A. Acc. Chem. Res. 1996, 29, 123.
12. (a) Han, H.; Wolfe, M. M.; Brenner, S.; Janda, K. D. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 6419.
13. (b) Han, H.; Janda, K. D. J. Am. Chem. Soc. 1996, 118, 2539.
14. Han, H.; Janda, K. D. J. Am. Chem. Soc. 1996, 118, 7632.
15. Graven, D. J.; Janda, K. D. Chem. Rev. 1997, 97, 489.
16. (e) Zhao, X.-Y.; Jung, K. W.; Janda, K. D. Tetrahedron Lett. 1997, 38, 977.
17. (f) Han, H.; Janda, K. D. Tetrahedron Lett. 1997, 38, 1527.
18. (a) Curran, D. P.; Hadida, S. 7. Am. Chem. Soc. 1996, 118, 2531.
19. (b) Studer, A.; Hadida, S.; Ferritto, R.; Kim, S.-Y.; Jeger, P.; Wipf, P.; Curran, D. P. Science 1997, 275, 823.
20. Corey, E. J.; Weinshenker, N. M.; Schaaf, T. K.; Huber, W. J. Am. Chem. Soc. 1969, 91, 5675.
21. (a) Sih, C. J.; Price, P.; Sood, R.; Salomon, R. G.; Peruzzotti, G.; Casey, M. J. Am. Chem. Soc. 1972, 94, 3643.
22. (b) Sato, F.; Tsujiyama, H.; Ono, N.; Yoshino, T.; Okamuko, S. Tetrahedron Lett. 1990, 4481.
23. (a) Noyori, R.; Suzuki, M. Chemlracts: Org. Chem. 1990, 173.
24. (b) Suzuki, M.; Monta, Y.; Koyano, H.; Koga, M.; Noyori, R. Tetrahedron 1990, 46, 4809.
25. (a) Gooding, O. W. J. Org. Chem. 1990, 55, 4209.
26. (b) Johnson, C. R.; Braun, M. P. J. Am. Chem. Soc. 1993, 115, 11014.
27. Lipshutz, B. H.; Wood, M. R. J. Am. Chem. Soc. 1994, 116, 11689.
28. 2 would entail utilization of an α-chain building block protected as an ester (i.e., trimethylsilyl ethyl) that could be cleanly removed under our subsequent deprotection conditions. Alternatively, methyl ester derivatives could be hydrolyzed by upases (See ref 8a and Tanaka, T.; Toru, T.; Okamura, N.; Hazato, A.; Sugiura, S.; Manabe, K.; Kurozumi, S.; Suzuki, M.; Kawagishi, T.; Noyori, R. Tetrahedron Lett. 1983, 24, 4103).
29. A review article (ref 3b) describes Ellman and CO-workers approach using insoluble matrices for the synthesis of prostaglandin analogues. See also: Thompson, L. A.; Ellman, J. A. 209th ACS National Meeting Anaheim, CA, 1995; Poster ORGN 262.
30. (a) Narita, M.; Hirata, M.; Kusano, K.; Itsuno, S.-L; Ue, M.; Okawara, M. Peptide Chemistry; Yonehara, H., Ed.; Protein Research Foundation: Osaka, 1979; pp 107-112.
31. (b) Narita, M. Bull, Chem. Soc. Jpn. 1978, 51, 1477.
32. (a) Fitch, W. L.; Detre, G.; Holmes, C. P.; Shoolery, J. N.; Keifer, P. A. J. Org. Chem. 1994, 59, 7955.
33. (b) Keifer, P. A. J. Org. Chem. 1996, 61, 1558.
34. Wehler, T.; Westman, J. Tetrahedron Lett. 1996, 37, 4771.
35. Pop, I. E.; Dhalluin, C. F.; Deprez, B. P.; Melnyk, P. C.; Lippens, G. M.; Tartar, A. L. Tetrahedron 1996, 52, 12209.
36. Thompson, L. A.; Ellman, J. A. Tetrahedron Lett. 1994, 35, 9333.
37. Paquette, L. A.; Earle, M. J.; Smith, G. F. Org. Synth. 1995, 73, 36.
38. Corey, E. J.; Niimura, K.; Konishi, Y.; Hashimoto, S.; Hamada, Y. Tetrahedron Lett. 1986, 27, 2199.
39. Casy, G.; Patterson, J. W.; Taylor, R. J. K. Org. Synth. 1993, Collect. Vol. VIII, 415.
40. Noyori, R.; Suzuki, M. Angew. Chem.. Int. Ed. Engl. 1984, 23, 847.
41. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; John Wiley & Sons, Inc.: New York, 1991; pp 31-34.
42. Newton, R. F.; Reynolds, D. P.; Finch, M. A. W.; Kelly, D. R.; Roberts, S. M. Tetrahedron Lett. 1979, 3981.
43. 2 methyl ester was obtained from Sigma Chemical.
44. Johnson, C. R.; Penning, T. D. J. Am. Chem. Soc. 1988, 770, 4726.
45. 2 methyl ester. We recovered 95% of the polymer mass through 9 at which stage 0.2 g was used for cleavage. This resulted in 7 mg of final purified PGEi methyl ester (18 mg theoretical) for a calculated yield of 37% (7 mg/18 mg × 0.95).