Macrocyclization on solid support using Heck reaction

Tetrahedron Letters

Volumn 38, Issue 29, 1997, Pages 5185-5188

  Akaji, Kenichi ^a   Kiso, Yoshiaki ^a  

^a KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

MACROCYCLIC COMPOUND; TETRAPEPTIDE;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; REACTION ANALYSIS; SYNTHESIS;

EID: 0030793233     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01123-4     Document Type: Article

References (20)

1. a) Thompson, L.A.; Ellman, J. A. Chem. Rev., 1996, 96, 555-600.
2. b) Gordon, E.M.; Gallop, M.A.; Patel, D.V. Acc. Chem. Res., 1996, 29, 144-154.
3. Mazur, S.; Jayalekshmy, P. J. Am. Chem. Soc., 1979, 101, 677-683.
4. a) Chen, L.; Barany, G. Lett. Peptide Sci., 1996, 3, 283-292.
5. b) Eritja, R.; Ziehler-Martin, J.P.; Walker, P.A.; Lee, T.D.; Legesse, K.; Albericio, F.; Kaplan, B.E. Tetrahedron, 1987, 43, 2675-2680.
6. Heck, R.F. Org. Reactions, 1982, 27, 345-390.
7. a) Hiroshige, M.; Hauske, J.R.; Zhou, P. J. Am. Chem. Soc., 1995, 117, 11590-11591.
8. b) Yu, K-L.; Deshpande, M.S.; Vyas, D.M. Tetrahedron Lett., 1994, 35, 8919-8922.
9. c) Jeffery, T. Tetrahedron Lett., 1994, 35, 3051-3054.
10. Ruoslahti, E.; Pierschbacher, M.D. Science, 1987, 238, 491-497.
11. a) Harada, T.; Katada, J.; Tachiki, A.; Asari, T.; Iijima, K.; Uno, I.; Ojima, I.; Hayashi, Y. Bioorg. Med. Chem. Lett., 1997, 7, 209-212.
12. b) McDowell, R.S.; Gadek, T.R.; Barker, P.L.; Burdick, D.J.; Chan, K.S.; Quan, C.L.; Skelton, N.; Struble, M.; Thorsett, E.D.; Tischler, M.; Tom, J.Y.K.; Webb, T.R.; Bumier, J.P. J. Am. Chem. Soc., 1994, 116, 5069-5076.
13. c) Jackson, S.; DeGrade, W.; Dwivedi, A.; Parthasarathy, A.; Higley, A.; Krywko, J.; Rockwell, A.; Markwalder, J.; Wells, G.; Wexler, R.; Mousa, S.; Harlow, R. J. Am. Chem. Soc., 1994, 116, 3220-3230.
14. Akaji, K.; Kuriyama, N.; Kiso, Y. J. Org. Chem., 1996, 61, 3350-3357.
15. a) Barlos, K.; Gatos, D.; Kallitsis, J.; Papaphotiu, G.; Sotiriu, P.; Wenqing, Y.; Schafer, W. Tetrahedron Lett., 1989, 30, 3943-3946.
16. b) Barlos, K.; Gatos, D.; Kapolos, S.; Papaphoutiu, G.; Schafer, W.; Wenqing, Y. Tetrahedron Lett., 1989, 30, 3947-3950.
17. α-Fmoc group was removed by 20 % piperidine/DMF (25°C, 20 min). Each coupling was conducted with Fmoc-amino acid, HOBt, and DIPCDI (2.5 equiv. each) in DMF at 25°C for 90 min. The coupling reaction was monitored by Kaiser ninhydrin test. Amino acid analysis after 12N HCl-propionic acid hydrolysis of 3: Asp 0.97, Gly 1.98, Arg 1.00.
18. 3CN (30 min) in 0.1 % aq.TFA, 0.9 ml/min.
19. 3N (9:1:1, 8 ml/g resin) were added in one portion. The mixture was agitated at 37°C for 4 h. The resin was filtered, washed extensively with DMF and MeOH, and dried in vacuo. Amino acid analysis after 12N HCl-propionic acid hydrolysis of the product: Asp 1.00, Gly 1.94, Arg 0.95.
20. 1H NMR analysis. Details of the configuration and conformational analysis of 7 will be published elsewhere.