Solid support synthesis of 14-membered macrocycles containing the thioether bridge via S(N)Ar methodology

Tetrahedron

Volumn 54, Issue 36, 1998, Pages 10635-10640

  Kiselyov, Alexander S ^a   Eisenberg, Shawn ^a   Luo, Ying ^a  

^a AMGEN INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 NITROBENZOIC ACID; CYSTEINE; FLUORINE; PIPERAZINE DERIVATIVE; SULFIDE;

ALKYLATION; ARTICLE; DRUG RESEARCH; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; SYNTHESIS;

EID: 0032480378     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00598-5     Document Type: Article

References (41)

1. 1. a) Balkenhohl, F.; von dem Bussche-Hunnefeld, C.; Lansky, A.; Zechel, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2288;
2. b) Kaldor, S.W.; Siegel, M.G. Curr. Opin. Chem. Biol. 1997, 1, 101;
3. c) Nefzi, A.; Ostresh, J.M.; Hougten, R.A. Chem. Rev. 1997, 97, 449;
4. d) Hermkens, P.H.H.; Ottenheijm, H.C.J.; Rees, D.C. Tetrahedron 1997, 53, 5643;
5. e) Thompson, L.A.; Ellman, J.A. Chem. Rev. 1996, 96, 555.
6. 2. a) Creswell, M.W.; Bolton, G.L.; Hodges, J.C.; Meppen, M. Tetrahedron 1998, 54, 3983; and references cited therein;
7. b) An, H.; Wang, T.; Mohan, V.; Griffey, R.H.; Cook, P.D. Tetrahedron 1998, 54, 3999;
8. c) Gustafson, G.R.; Baldino, C.M.; O'Donnel, M.-M. E.; Sheldon, A.; Tarsa, R.J.; Verni, C.J.; Coffen, D.L. Tetrahedron 1998, 54, 4051;
9. d) Kiselyov, A.S.; Smith, L.; Armstrong, R. Tetrahedron 1998, 54, 5089; and references cited therein.
10. 3. a) Armstrong, R.W.; Brown, S.D.; Keating, T.A.; Tempest, P.A. Combinatorial Chemistry, Synthesis and Application, Ed. by S.R. Wilson and A.W. Czarnik, Wiley-Interscience, New York 1997, 153;
11. b) Kiselyov, A.S.; Armstrong, R.W. Tetrahedron Lett. 1997, 38, 6163.
12. 4. Pyluck, A.; Yuan, R.; Galligan, E.; Primakoff, P.; Myles, D.G.; Sampson, N.S. Bioorg. Med. Chem. Letters 1997, 7, 1053.
13. 5. For a recent review on the design and synthesis of conformationally constrained amino acids, including β-turn mimetics, see Hanessian, S.; McNaughton-Smith, G.; Lombart, H.-G.; Lubell, W.D. Tetrahedron 1997, 53, 12789, and references cited therein.
14. a) Virgilio, A.; Ellman, J. J. Am. Chem. Soc. 1994, 116, 11580;
15. b) Virgilio, A.; Bray, A.A.; Zhang, W.; Trinh, L.; Snyder, M.; Morrissey, M.M.; Ellman, J.A. Tetrahedron 1997, 53, 6635;
16. c) Virgilio, A.A.; Schurer, S.C.; Ellman, J.A. Tetrahedron Lett. 1996, 37, 6961.
17. 6. a) Zhu, J. SynLett 1997, 133 and references cited therein;
18. b) Gonzalez, G.I.; Zhu, J.P.J. Org. Chem. 1997, 62, 7544;
19. c) Zhu, J.P.; Laib, T.; Chastanet, J.; Beugelmans, R. Angew, Chem., Int. Ed. Engl. 1996, 35, 2517.
20. 7. For the biological activity of representative examples of macrocycles containing the biaryl ether bridge, see for example: a) Glycopeptide Antibiotics, Ed. R. Nagarajan, Dekker, New York, 1994;
21. K-13: b) Yasuzawa, T.; Shirahata, K.; Sano, H. J. Antibiot. 1987, 40, 455;
22. c) Kase, H.; Kaneko, M.; Yamada, K. J. Antibiot. 1987, 40, 450;
23. OF4949 I-IV: d) Sano, S.; Ikai, K.; Kuroda, H.; Nakamura, T.; Obayashi, A.; Ezure, Y.; Enomoto, H. J. Antibiot. 1986, 39, 1674;
24. Piperazinomycin: e) Tamai, S.; Kaneda, M.; Nakamura, S. J. Antibiot. 1982, 35, 1130;
25. deoxybouvardin: f) Jolad, S.D.; Hoffmann, J.J.; Torrance, S.J.; Wiedhopf, R.M.; Cole, J.R.; Arora, S.K.; Bates, R.B.; Gargiulo, R.L.; Kriek, G.R. J. Am. Chem. Soc. 1977, 99, 8040;
26. g) ristocetin: Harris, C.M.; Kibby, J.J.; Fehlner, J.R.; Raabe, A.B.; Barber, T.A.; Harris, T.M. J. Am. Chem. Soc. 1979, 101, 437;
27. h) actaplanin: Hunt, A.H.; Debono, M.; Merkel, K.E.; Barnhart, M. J. Org. Chem. 1984, 49, 635;
28. i) b-avoparcin: McGahren, W.J.; Martin, J.H.; Morton, G.O.; Hargreaves, R.T.; Leese, R.A.; Lovell, F.M.; Ellestad, G.A.; O'Brien, E.; Holker, J.S.E. J. Am. Chem. Soc. 1980, 102, 1671;
29. vancomycin: j) Walsh, C.T. Science 1993, 261, 308;
30. k) Bugg, T.D.H.; Dutka-Malen, S.; Arthur, M.; Courvalin, P.; Walsh, C.T. Biochemistry 1991, 30, 2017
31. NAr, see for example: (a) Terrier, F. Nucleophilic Aromatic Displacement: The Role of the Nitro Group; VCH: New York, 1991, chapter 1;
32. (b) Paradisi, C. Arene Substitution via Nucleophilic Addition to Electron Deficient Arenes. Comprehensive Organic Synthesis; Trost, B.M.; Flaming, I., Eds. Pergamon Press: Oxford, 1991, Vol 4, 423;
33. (c) Artamkina, G.A.; Egorov, M.P.; Beletskaya, I.P. Chem. Rev. 1982, 82, 427.
34. 9. a) Burgess, K.; Lim, D.; Bois-Choussy, M.; Zhu, J. Tetrahedron Lett. 1997, 38, 3345;
35. b) Feng, Y.; Wang, Z.; Burgess, K. Books of Abstracts, 215h ACS National Meeting, Part 2, ACS, Dallas, 1998, 054;
36. c) Zhang, A.J.; Burgess, K. Books of Abstracts, 215th ACS National Meeting, Part 2, ACS, Dallas, 1998, 246;
37. d) Svensson, A.; Fex, T.; Kihlberg, J. 1996, 37, 7649.
38. 10. Kamm, O.; Matthews, A.O. Org. Syn. Col. Vol. 1 1941, 392.
39. 11. Ouyang, S.; Armstrong, R.W.; Murphy, M. J. Org. Chem. 1998, 63, 1027.
40. 12. Zukermann, R.N.; Martin, E.J.; Spellmeyer, D.C.; Stauber, G.B.; Shoemaker, K.R.; Kerr, J.M.; Figliozzi, G.M.; Goff, D.A.; Siani, M.A.; Simon, R.J.; Banville, S.C.; Brown, E.G.; Wang, L.; Richter, L.S.; Moos, W.H. J. Med. Chem. 1994, 37, 2678.
41. 13. Carpino, L.A. J. Am. Chem. Soc. 1993, 115, 4397.