A second generation solid phase approach to Freidinger lactams: Application of Fukuyama's amine synthesis and cyclative release via ring closing metathesis

Tetrahedron Letters

Volumn 39, Issue 18, 1998, Pages 2667-2670

  Piscopio, Anthony D ^a   Miller, John F ^a   Koch, Kevin ^a  

^a AMGEN INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; LACTAM DERIVATIVE;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0032580351     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00374-8     Document Type: Article

References (27)

1. 1. Piscopio, A.D.; Miller, J.F.; Koch, K. Tetrahedron Lett. 1997, 38, 7143-7146.
2. 2. Reviews: (a) Hermkins, P. H. H.; Ottenheijm, H. C. J.; Rees, D. Tetrahedron 1996, 52, 4527-4554.
3. (b) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555-600.
4. (c) Gallop, M. A.; Barret, R. W.; Dower, W. J.; Foder, S. P.; Gorden, E. M. J. Med. Chem. 1994, 37, 1233-1251.
5. (d) Gorden, E. M.; Barret, R. W.; Dower, W. J.; Foder, S. P.; Gallop, M. A. J. Med. Chem. 1994, 37, 1385-1401.
6. (e) Moos, W.H.; Green, G. D.; Pavia, M. R. Annu. Report Med. Chem. 1993, 28, 315-324.
7. (f) Leznoff, C. C. Acc. Chem. Res. 1978, 11 327-333.
8. (g) Crowley, J.I.; Rapaport, H. Acc. Chem. Res. 1976, 9, 135-144.
9. 3. For pioneering work in the area of polymer supported synthesis see: (a) Merrifield, R B. J. Ant. Chem. Soc. 1963, 85, 2149.
10. (b) Merrifield, R. B. J. Am. Chem. Soc. 1963, 85, 3045.
11. 4. (a) Freidinger, R. M.; Verber, D.F.; Schwenk Perlow, D.; Brooks, J. R. Saperstein, R. Science, 1980, 210, 656.
12. (b) Freidmger, R. M.; Schwenk Perlow, D.; Verber, D. F. J. Org. Chem. 1982, 47, 104.
13. 5. For an excellent review on peptidomimetics see: Liskamp, R.M.J. Recl. Trav. Chim. Pays-Bas 1994, 113, 1-19.
14. 6. (a) Cheung, M.; Jow, C.-K.; Fukuyama, T. Book of Abstracts, 211th ACS Meeting New Orleans, La. March 24-28, 1996, ORG-215 ACS, Washington D.C.
15. (b) Fukuyama, T.; Cheung, M.; Jow, C.-K.; Hidai, Y.; Kan, T. Tetrahedron Lett. 1997, 38, 5831-5834.
16. 7. Mitsunobu, O. Synthesis, 1981, 1-28.
17. 8. (a) Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100-110.
18. (b) Miller, S. J.; Kim, S.-H.; Chen, Z.-R.; Grubbs, R. H. Ibid 1995, 117, 2108-2109.
19. (c) Fujimura, O.; Fu, G. C.; Grubbs, R. H. J. Org. Chem. 1994, 59, 4029-4031.
20. (d) Fu, G. C.; Grubbs, R. H. J. Am. Chem. Soc. 1992, 114, 5426-5427.
21. 9. Based on recovered N-(n-Butyl)-2,4-dinitroaniline from sulfonamide removal with n-butylamine (assumes quantitative cleavagt): see reference 6.
22. 10. (S)-Ally1 glycine ahd (S)-methyl-2-hydroxy-3-phenyl propionate were used and a single diastereomeric product (8) was obtained, presumably with inversion of configuration during the loading step.
23. 6 (5-10%) when HATU was used despite rigorous washing of the resin following acylation, and tricyclohexylphosphine oxide < 5%.
24. 12. Frechet, J. M.; Schuerch, C. J. J. Am. Chem. Soc. 1971, 93, 492-496.
25. 13. The amount of recovered of 13 indicated a quantitative conversion of 10 to 12 and I.R. analysis of of resin 5 following TFA treatment indicated a complete disappearance of the characteristic carbonyl stretch.
26. 14. HATU and PyBroP gave similar yields. However, while the less reactive PyBroP required longer reaction times, desired products were obtained free of ammonium salts (see reference 11).
27. 15. Based on solution phase model studies using trans-einnamyl amine.