Stereocontrolled solid-phase synthesis of fluorinated partially-modified retropeptides via tandem aza-Michael/enolate-protonation

Tetrahedron Letters

Volumn 44, Issue 37, 2003, Pages 7019-7022

  Volonterio, Alessandro ^a   Chiva, Gema ^b   Fustero, Santos ^b   Piera, Julio ^b   Sanchez Rosello, Maria ^b   Sani, Monica ^c   Zanda, Matteo ^c  

^a Dipartimento di Chimica   (Italy)

^b UNIVERSITY OF VALENCIA   (Spain)

^c CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 DIAZABICYCLO[2.2.2]OCTANE; 2 TRIFLUOROMETHYLPROPENOYL CHLORIDE; ACRYLIC ACID DERIVATIVE; ALANINE DERIVATIVE; AMINO ACID DERIVATIVE; BASE; CARBON TETRACHLORIDE; PEPTIDE DERIVATIVE; RESIN; SOLVENT; TRIFLUOROALANINE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; FLUORINATION; MICHAEL ADDITION; PROTON TRANSPORT; SOLID; STEREOCHEMISTRY; SYNTHESIS;

EID: 0043160153     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01787-8     Document Type: Article

References (35)

1. Olson G.L., Bolin D.R., Bonner M.P., Bös M., Cook C.M., Fry D.C., Graves B.J., Hatada M., Hill D.E., Kahn M., Madison V.S., Rusiecki V.K., Sarabu R., Sepinwall J., Vincent G.P., Voss M.E. J. Med. Chem. 36:1993;3039-3049.
2. Gante J. Angew. Chem., Int. Ed. Engl. 33:1994;1699-1720.
3. Leung D., Abbenante G., Fairlie D.P. J. Med. Chem. 43:2000;305-341.
4. Fletcher M.D., Campbell M.M. Chem. Rev. 98:1998;763-795.
5. Chorev M., Goodman M. Acc. Chem. Res. 26:1993;266-273.
6. Chorev M., Goodman M. Trends Biotechnol. 13:1995;438-445.
7. Volonterio A., Bravo P., Zanda M. Org. Lett. 2:2000;1827-1830.
8. Volonterio A., Bravo P., Zanda M. Tetrahedron Lett. 42:2001;3141-3144.
9. Volonterio A., Bellosta S., Bravo P., Canavesi M., Corradi E., Meille S.V., Monetti M., Moussier N., Zanda M. Eur. J. Org. Chem. 2002;428-438 Volonterio, A.; Bellosta, S.; Bravin, F.; Bellucci, M. C.; Bruché, L.; Colombo, G.; Malpezzi, L.; Mazzini, S.; Meille, S. V.; Meli, M.; Ramírez de Arellano, C.; Zanda, M. Chem. Eur. J. 2003, accepted for publication.
10. Volonterio A., Bellosta S., Bravo P., Canavesi M., Corradi E., Meille S.V., Monetti M., Moussier N., Zanda M. Eur. J. Org. Chem. 2002;428-438 Volonterio, A.; Bellosta, S.; Bravin, F.; Bellucci, M. C.; Bruché, L.; Colombo, G.; Malpezzi, L.; Mazzini, S.; Meille, S. V.; Meli, M.; Ramírez de Arellano, C.; Zanda, M. Chem. Eur. J. 2003, accepted for publication.
11. Höss, E.; Rudolph, M.; Seymour, L.; Schierlinger, C.; Burger, K. J. Fluorine Chem. 1993, 61, 163-170 and references therein.
12. Osipov S.N., Sewald N., Kolomiets A.F., Fokin A.V., Burger K. Tetrahedron Lett. 37:1996;615-618.
13. Bordusa F., Dahl C., Jakubke H.-D., Burger K., Koksch B. Tetrahedron: Asymmetry. 10:1999;307-313.
14. Fluorine-containing Amino Acids, Synthesis and Properties; Kukhar', V. P.; Soloshonok, V A. Eds.; Wiley: Chichester, 1995.
15. Lebouvier N., Laroche C., Huguenot F., Brigaud T. Tetrahedron Lett. 43:2002;2827-2830.
16. Sakai T., Yan F., Kashino S., Uneyama K. Tetrahedron. 52:1996;233-244.
17. Ayhan S., Demir A.S., Özge S., Zuhal G.-A. Tetrahedron: Asymmetry. 12:2001;2309-2313.
18. Fustero S., Navarro A., Pina B., Soler J.G., Bartolomé A., Asensio A., Simón A., Bravo P., Fronza G., Volonterio A., Zanda M. Org. Lett. 3:2001;2621-2624.
19. Sani M., Bruché L., Chiva G., Fustero S., Piera J., Volonterio A., Zanda M. Angew. Chem. Int. Ed. 42:2003;2060-2063.
20. See, for example: (a) Hutchison, P. C.; Heightman, T. D.; Procter, D. J. Org. Lett. 2002, 4, 4583-4585 and references therein; (b) Nagashima, T.; Davies, H. M. L. J. Am. Chem. Soc. 2001, 123, 2695-2696; c) Xia, Y.; Yang, Z.-Y.; Brossi, A.; Lee, K.-H. Org. Lett. 1999, 1, 2113-2115; (d) Myers, A. G.; Lanman, B. A. J. Am. Chem. Soc. 2002, 124, 12969-12971; (e) Oertel, K.; Zech, G.; Kunz, H. Angew. Chem., Int. Ed. 2000, 39, 1431-1433; (f) Annis, D. A.; Helluin, O.; Jacobsen, E. N. Angew. Chem., Int. Ed. 1998, 37, 1907-1909; (g) Furman, B.; Thürmer, R.; Kaluza, Z.; Lysek, R.; Voelter, W.; Chmielewski, M. Angew. Chem., Int. Ed. 1999, 38, 1121-1123; (h) Delpiccolo, C. M. L.; Mata, E. G. Tetrahedron: Asymmetry 2002, 13, 905-910; (i) Dujardin, G.; Leconte, S.; Coutable, L.; Brown, E. Tetrahedron Lett. 2001, 42, 8849-8852; (j) Hanessian, S.; Bayrakdarian, M. Tetrahedron Lett. 2002, 43, 9441-9444; (k) Zou, N.; Jiang, B. J. Comb. Chem. 2000, 2, 6-7.
21. See, for example: (a) Hutchison, P. C.; Heightman, T. D.; Procter, D. J. Org. Lett. 2002, 4, 4583-4585 and references therein; (b) Nagashima, T.; Davies, H. M. L. J. Am. Chem. Soc. 2001, 123, 2695-2696; c) Xia, Y.; Yang, Z.-Y.; Brossi, A.; Lee, K.-H. Org. Lett. 1999, 1, 2113-2115; (d) Myers, A. G.; Lanman, B. A. J. Am. Chem. Soc. 2002, 124, 12969-12971; (e) Oertel, K.; Zech, G.; Kunz, H. Angew. Chem., Int. Ed. 2000, 39, 1431-1433; (f) Annis, D. A.; Helluin, O.; Jacobsen, E. N. Angew. Chem., Int. Ed. 1998, 37, 1907-1909; (g) Furman, B.; Thürmer, R.; Kaluza, Z.; Lysek, R.; Voelter, W.; Chmielewski, M. Angew. Chem., Int. Ed. 1999, 38, 1121-1123; (h) Delpiccolo, C. M. L.; Mata, E. G. Tetrahedron: Asymmetry 2002, 13, 905-910; (i) Dujardin, G.; Leconte, S.; Coutable, L.; Brown, E. Tetrahedron Lett. 2001, 42, 8849-8852; (j) Hanessian, S.; Bayrakdarian, M. Tetrahedron Lett. 2002, 43, 9441-9444; (k) Zou, N.; Jiang, B. J. Comb. Chem. 2000, 2, 6-7.
22. See, for example: (a) Hutchison, P. C.; Heightman, T. D.; Procter, D. J. Org. Lett. 2002, 4, 4583-4585 and references therein; (b) Nagashima, T.; Davies, H. M. L. J. Am. Chem. Soc. 2001, 123, 2695-2696; c) Xia, Y.; Yang, Z.-Y.; Brossi, A.; Lee, K.-H. Org. Lett. 1999, 1, 2113-2115; (d) Myers, A. G.; Lanman, B. A. J. Am. Chem. Soc. 2002, 124, 12969-12971; (e) Oertel, K.; Zech, G.; Kunz, H. Angew. Chem., Int. Ed. 2000, 39, 1431-1433; (f) Annis, D. A.; Helluin, O.; Jacobsen, E. N. Angew. Chem., Int. Ed. 1998, 37, 1907-1909; (g) Furman, B.; Thürmer, R.; Kaluza, Z.; Lysek, R.; Voelter, W.; Chmielewski, M. Angew. Chem., Int. Ed. 1999, 38, 1121-1123; (h) Delpiccolo, C. M. L.; Mata, E. G. Tetrahedron: Asymmetry 2002, 13, 905-910; (i) Dujardin, G.; Leconte, S.; Coutable, L.; Brown, E. Tetrahedron Lett. 2001, 42, 8849-8852; (j) Hanessian, S.; Bayrakdarian, M. Tetrahedron Lett. 2002, 43, 9441-9444; (k) Zou, N.; Jiang, B. J. Comb. Chem. 2000, 2, 6-7.
23. See, for example: (a) Hutchison, P. C.; Heightman, T. D.; Procter, D. J. Org. Lett. 2002, 4, 4583-4585 and references therein; (b) Nagashima, T.; Davies, H. M. L. J. Am. Chem. Soc. 2001, 123, 2695-2696; c) Xia, Y.; Yang, Z.-Y.; Brossi, A.; Lee, K.-H. Org. Lett. 1999, 1, 2113-2115; (d) Myers, A. G.; Lanman, B. A. J. Am. Chem. Soc. 2002, 124, 12969-12971; (e) Oertel, K.; Zech, G.; Kunz, H. Angew. Chem., Int. Ed. 2000, 39, 1431-1433; (f) Annis, D. A.; Helluin, O.; Jacobsen, E. N. Angew. Chem., Int. Ed. 1998, 37, 1907-1909; (g) Furman, B.; Thürmer, R.; Kaluza, Z.; Lysek, R.; Voelter, W.; Chmielewski, M. Angew. Chem., Int. Ed. 1999, 38, 1121-1123; (h) Delpiccolo, C. M. L.; Mata, E. G. Tetrahedron: Asymmetry 2002, 13, 905-910; (i) Dujardin, G.; Leconte, S.; Coutable, L.; Brown, E. Tetrahedron Lett. 2001, 42, 8849-8852; (j) Hanessian, S.; Bayrakdarian, M. Tetrahedron Lett. 2002, 43, 9441-9444; (k) Zou, N.; Jiang, B. J. Comb. Chem. 2000, 2, 6-7.
24. See, for example: (a) Hutchison, P. C.; Heightman, T. D.; Procter, D. J. Org. Lett. 2002, 4, 4583-4585 and references therein; (b) Nagashima, T.; Davies, H. M. L. J. Am. Chem. Soc. 2001, 123, 2695-2696; c) Xia, Y.; Yang, Z.-Y.; Brossi, A.; Lee, K.-H. Org. Lett. 1999, 1, 2113-2115; (d) Myers, A. G.; Lanman, B. A. J. Am. Chem. Soc. 2002, 124, 12969-12971; (e) Oertel, K.; Zech, G.; Kunz, H. Angew. Chem., Int. Ed. 2000, 39, 1431-1433; (f) Annis, D. A.; Helluin, O.; Jacobsen, E. N. Angew. Chem., Int. Ed. 1998, 37, 1907-1909; (g) Furman, B.; Thürmer, R.; Kaluza, Z.; Lysek, R.; Voelter, W.; Chmielewski, M. Angew. Chem., Int. Ed. 1999, 38, 1121-1123; (h) Delpiccolo, C. M. L.; Mata, E. G. Tetrahedron: Asymmetry 2002, 13, 905-910; (i) Dujardin, G.; Leconte, S.; Coutable, L.; Brown, E. Tetrahedron Lett. 2001, 42, 8849-8852; (j) Hanessian, S.; Bayrakdarian, M. Tetrahedron Lett. 2002, 43, 9441-9444; (k) Zou, N.; Jiang, B. J. Comb. Chem. 2000, 2, 6-7.
25. See, for example: (a) Hutchison, P. C.; Heightman, T. D.; Procter, D. J. Org. Lett. 2002, 4, 4583-4585 and references therein; (b) Nagashima, T.; Davies, H. M. L. J. Am. Chem. Soc. 2001, 123, 2695-2696; c) Xia, Y.; Yang, Z.-Y.; Brossi, A.; Lee, K.-H. Org. Lett. 1999, 1, 2113-2115; (d) Myers, A. G.; Lanman, B. A. J. Am. Chem. Soc. 2002, 124, 12969-12971; (e) Oertel, K.; Zech, G.; Kunz, H. Angew. Chem., Int. Ed. 2000, 39, 1431-1433; (f) Annis, D. A.; Helluin, O.; Jacobsen, E. N. Angew. Chem., Int. Ed. 1998, 37, 1907-1909; (g) Furman, B.; Thürmer, R.; Kaluza, Z.; Lysek, R.; Voelter, W.; Chmielewski, M. Angew. Chem., Int. Ed. 1999, 38, 1121-1123; (h) Delpiccolo, C. M. L.; Mata, E. G. Tetrahedron: Asymmetry 2002, 13, 905-910; (i) Dujardin, G.; Leconte, S.; Coutable, L.; Brown, E. Tetrahedron Lett. 2001, 42, 8849-8852; (j) Hanessian, S.; Bayrakdarian, M. Tetrahedron Lett. 2002, 43, 9441-9444; (k) Zou, N.; Jiang, B. J. Comb. Chem. 2000, 2, 6-7.
26. See, for example: (a) Hutchison, P. C.; Heightman, T. D.; Procter, D. J. Org. Lett. 2002, 4, 4583-4585 and references therein; (b) Nagashima, T.; Davies, H. M. L. J. Am. Chem. Soc. 2001, 123, 2695-2696; c) Xia, Y.; Yang, Z.-Y.; Brossi, A.; Lee, K.-H. Org. Lett. 1999, 1, 2113-2115; (d) Myers, A. G.; Lanman, B. A. J. Am. Chem. Soc. 2002, 124, 12969-12971; (e) Oertel, K.; Zech, G.; Kunz, H. Angew. Chem., Int. Ed. 2000, 39, 1431-1433; (f) Annis, D. A.; Helluin, O.; Jacobsen, E. N. Angew. Chem., Int. Ed. 1998, 37, 1907-1909; (g) Furman, B.; Thürmer, R.; Kaluza, Z.; Lysek, R.; Voelter, W.; Chmielewski, M. Angew. Chem., Int. Ed. 1999, 38, 1121-1123; (h) Delpiccolo, C. M. L.; Mata, E. G. Tetrahedron: Asymmetry 2002, 13, 905-910; (i) Dujardin, G.; Leconte, S.; Coutable, L.; Brown, E. Tetrahedron Lett. 2001, 42, 8849-8852; (j) Hanessian, S.; Bayrakdarian, M. Tetrahedron Lett. 2002, 43, 9441-9444; (k) Zou, N.; Jiang, B. J. Comb. Chem. 2000, 2, 6-7.
27. See, for example: (a) Hutchison, P. C.; Heightman, T. D.; Procter, D. J. Org. Lett. 2002, 4, 4583-4585 and references therein; (b) Nagashima, T.; Davies, H. M. L. J. Am. Chem. Soc. 2001, 123, 2695-2696; c) Xia, Y.; Yang, Z.-Y.; Brossi, A.; Lee, K.-H. Org. Lett. 1999, 1, 2113-2115; (d) Myers, A. G.; Lanman, B. A. J. Am. Chem. Soc. 2002, 124, 12969-12971; (e) Oertel, K.; Zech, G.; Kunz, H. Angew. Chem., Int. Ed. 2000, 39, 1431-1433; (f) Annis, D. A.; Helluin, O.; Jacobsen, E. N. Angew. Chem., Int. Ed. 1998, 37, 1907-1909; (g) Furman, B.; Thürmer, R.; Kaluza, Z.; Lysek, R.; Voelter, W.; Chmielewski, M. Angew. Chem., Int. Ed. 1999, 38, 1121-1123; (h) Delpiccolo, C. M. L.; Mata, E. G. Tetrahedron: Asymmetry 2002, 13, 905-910; (i) Dujardin, G.; Leconte, S.; Coutable, L.; Brown, E. Tetrahedron Lett. 2001, 42, 8849-8852; (j) Hanessian, S.; Bayrakdarian, M. Tetrahedron Lett. 2002, 43, 9441-9444; (k) Zou, N.; Jiang, B. J. Comb. Chem. 2000, 2, 6-7.
28. See, for example: (a) Hutchison, P. C.; Heightman, T. D.; Procter, D. J. Org. Lett. 2002, 4, 4583-4585 and references therein; (b) Nagashima, T.; Davies, H. M. L. J. Am. Chem. Soc. 2001, 123, 2695-2696; c) Xia, Y.; Yang, Z.-Y.; Brossi, A.; Lee, K.-H. Org. Lett. 1999, 1, 2113-2115; (d) Myers, A. G.; Lanman, B. A. J. Am. Chem. Soc. 2002, 124, 12969-12971; (e) Oertel, K.; Zech, G.; Kunz, H. Angew. Chem., Int. Ed. 2000, 39, 1431-1433; (f) Annis, D. A.; Helluin, O.; Jacobsen, E. N. Angew. Chem., Int. Ed. 1998, 37, 1907-1909; (g) Furman, B.; Thürmer, R.; Kaluza, Z.; Lysek, R.; Voelter, W.; Chmielewski, M. Angew. Chem., Int. Ed. 1999, 38, 1121-1123; (h) Delpiccolo, C. M. L.; Mata, E. G. Tetrahedron: Asymmetry 2002, 13, 905-910; (i) Dujardin, G.; Leconte, S.; Coutable, L.; Brown, E. Tetrahedron Lett. 2001, 42, 8849-8852; (j) Hanessian, S.; Bayrakdarian, M. Tetrahedron Lett. 2002, 43, 9441-9444; (k) Zou, N.; Jiang, B. J. Comb. Chem. 2000, 2, 6-7.
29. See, for example: (a) Hutchison, P. C.; Heightman, T. D.; Procter, D. J. Org. Lett. 2002, 4, 4583-4585 and references therein; (b) Nagashima, T.; Davies, H. M. L. J. Am. Chem. Soc. 2001, 123, 2695-2696; c) Xia, Y.; Yang, Z.-Y.; Brossi, A.; Lee, K.-H. Org. Lett. 1999, 1, 2113-2115; (d) Myers, A. G.; Lanman, B. A. J. Am. Chem. Soc. 2002, 124, 12969-12971; (e) Oertel, K.; Zech, G.; Kunz, H. Angew. Chem., Int. Ed. 2000, 39, 1431-1433; (f) Annis, D. A.; Helluin, O.; Jacobsen, E. N. Angew. Chem., Int. Ed. 1998, 37, 1907-1909; (g) Furman, B.; Thürmer, R.; Kaluza, Z.; Lysek, R.; Voelter, W.; Chmielewski, M. Angew. Chem., Int. Ed. 1999, 38, 1121-1123; (h) Delpiccolo, C. M. L.; Mata, E. G. Tetrahedron: Asymmetry 2002, 13, 905-910; (i) Dujardin, G.; Leconte, S.; Coutable, L.; Brown, E. Tetrahedron Lett. 2001, 42, 8849-8852; (j) Hanessian, S.; Bayrakdarian, M. Tetrahedron Lett. 2002, 43, 9441-9444; (k) Zou, N.; Jiang, B. J. Comb. Chem. 2000, 2, 6-7.
30. See, for example: (a) Hutchison, P. C.; Heightman, T. D.; Procter, D. J. Org. Lett. 2002, 4, 4583-4585 and references therein; (b) Nagashima, T.; Davies, H. M. L. J. Am. Chem. Soc. 2001, 123, 2695-2696; c) Xia, Y.; Yang, Z.-Y.; Brossi, A.; Lee, K.-H. Org. Lett. 1999, 1, 2113-2115; (d) Myers, A. G.; Lanman, B. A. J. Am. Chem. Soc. 2002, 124, 12969-12971; (e) Oertel, K.; Zech, G.; Kunz, H. Angew. Chem., Int. Ed. 2000, 39, 1431-1433; (f) Annis, D. A.; Helluin, O.; Jacobsen, E. N. Angew. Chem., Int. Ed. 1998, 37, 1907-1909; (g) Furman, B.; Thürmer, R.; Kaluza, Z.; Lysek, R.; Voelter, W.; Chmielewski, M. Angew. Chem., Int. Ed. 1999, 38, 1121-1123; (h) Delpiccolo, C. M. L.; Mata, E. G. Tetrahedron: Asymmetry 2002, 13, 905-910; (i) Dujardin, G.; Leconte, S.; Coutable, L.; Brown, E. Tetrahedron Lett. 2001, 42, 8849-8852; (j) Hanessian, S.; Bayrakdarian, M. Tetrahedron Lett. 2002, 43, 9441-9444; (k) Zou, N.; Jiang, B. J. Comb. Chem. 2000, 2, 6-7.
31. Hanzawa Y., Suzuki M., Kobayashi Y., Taguchi T., Iitaka Y. J. Org. Chem. 56:1991;1718-1725.
32. Yamazaki T., Ichige T., Takei S., Kawashita S., Kitazume T., Kubota T. Org. Lett. 3:2001;2915-2918.
33. General experimental procedure for the preparation of resins 4 . To a suspension of resin 3 in dry DCM neat sym-collidine (1 equiv. based on the theoretical loading of 3 ) followed by a solution of 2-trifluoromethyl propenoyl chloride (3 equiv.) in dry DCM were added under nitrogen atmosphere at 0°C. The suspension was stirred for 1 hour at rt and then filtered. The resin 4 was washed with DMF (×3) and DCM (×5), then the residual solvent was removed at reduced pressure.
34. 2 (×3), and MeOH (×3), then the residual solvent was removed at reduced pressure.
35. 4 system afforded products 6b-n with slightly lower purities than those featured by the TMP/DCM system.