Solid support synthesis of 14-membered macrocycles via S(N)AR methodology on acrylate resin

Tetrahedron Letters

Volumn 40, Issue 13, 1999, Pages 2465-2468

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

^a AMGEN INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLIC ACID RESIN; BROMOACETIC ACID; DOPA; K 13; MACROCYCLIC COMPOUND; PIPERAZINE; TEICOPLANIN; VANCOMYCIN;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; PEPTIDE SYNTHESIS; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0033605867     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00278-6     Document Type: Article

References (45)

1. Glycopeptide Antibiotics, Ed. R. Nagarajan, Dekker, New York, 1994.
2. K-13: (a) Yasuzawa, T.; Shirahata, K.; Sano, H. J. Antibiot. 1987, 40, 455;
3. OF4949 I-IV: (b) Sano, S.; Ikai, K.; Kuroda, H.; Nakamura, T.; Obayashi, A.; Ezure, Y.; Enomoto, H. J. Antibiot. 1986, 39, 1674.
4. Piperazinomycin: (a) Tamai, S.; Kaneda, M.; Nakamura, S. J. Antibiot. 1982, 35, 1130;
5. hexapeptide RA antibiotics: (b) Itokawa, H., Takeya, K. Heterocycles 1993, 35, 1467;
6. deoxybouvardin: (c) 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.
7. (a) Gerhard, U.; Mackay, J.P.; Maplestone, R.A.; Williams, D.H. J.Am.Chem.Soc. 1993, 115, 232;
8. (b) Sheldrick, G.M.; Jones, P.J.; Kennard, O.; Williams, D.H.; Smith, G.A. Nature 1978, 271, 223;
9. (c) Walsh, C.T. Science 1993, 261, 305.
10. (a) Barna, J.C.J.; Williams, D.H.; Stone, D.J.M.; Leung, T.W.C.; Doddrell, D.M. J.Am.Chem.Soc. 1984, 106, 4895;
11. a number of related glycopeptide antibiotics have been isolated, see for example: i) 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;
12. ii) actaplanin: Hunt, A.H.; Debono, M.; Merkel, K.E.; Barnhart, M. J.Org.Chem. 1984, 49, 635;
13. iii) 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.
14. (a) Lamont, R.B.; Allen, D.G.; Clemens, I.R.; Newall, C.E.; Ramsay, M.V.J.; Rose, M.; Fortt, S.; Gallagher, T. J.Chem.Soc., Chem. Commun. 1992, 1693;
15. (b) Hobbs, D.W.; Still, W.C. Tetrahedron Lett. 1987, 28, 2805;
16. (c) Dushin, R.G.; Danishefsky, S.J. J.Am.Chem.Soc. 1992, 114, 3471;
17. d) Chakraborty, T.K.; Reddy, G.V. J.Org.Chem. 1992, 57, 5462.
18. (a) Rama Rao, A.V.; Gurjar, M.K.; Reddy, L.; Rao, A.S. Chem.Rev. 1995, 95, 2135, and references cited therein;
19. (b) Pearson, A.J.; Bignan, G.; Zhang, P.; Chelliah, M. J.Org.Chem. 1996, 61, 3940.
20. (a) Suzuki, Y.; Nishiyama, S.; Yamamura, S. Tetrahedron Lett. 1989, 30, 6043;
21. (d) Inoue, T.; Sasaki, T.; Takayanagi, H.; Harigaya, Y.; Hoshino, O.; Hara, H.; Inaba, T. J.Org.Chem. 1996, 61, 3936.
22. (a) Evans, D.A.; Barrow, J.C.; Watson, P.S.; Ratz, A.M.; Dinsmore, C.J.; Evrard, D.A.; DeVries, K.M.; Ellman, J.A.; Rychnowsky, S.D.; Lacour, J. J.Am.Chem.Soc. 1997, 119, 3419;
23. (b) Evans, D.A.; Dinsmore, C.J.; Ratz, A.M.; Evrard, D.A.; Barrow, J.C. J.Am.Chem.Soc. 1997, 119, 3417.
24. (a) Boger, D.L.; Yohannes, D.; Zhou, J.; Patane, M.A. J.Am.Chem.Soc. 1993, 115, 3420;
25. (b) Boger, D.L.; Borzilleri, R.M.; Nukui, S.; Beresis, R.T. J.Org.Chem. 1997, 62, 4721.
26. (a) Zhu, J. Synlett 1997, 133 and references cited therein;
27. (b) Gonzalez, G.I.; Zhu, J.P. J.Org.Chem. 1997, 62, 7544.
28. Rao, A.V.R.; Reddy, K.L.; Rao, A.S. Tetrahedron Lett. 1994, 35, 8465.
29. Janetka, J.W.; Rich, D.H. J.Am.Chem.Soc. 1995, 117, 10585.
30. (a) Nicolaou, K.C.; Ramanjulu, J.M.; Natarajan, S.; Brase, S.; Li, H.; Boddy, C.N.C. J.Chem.Soc., Chem.Commun. 1997, 1899;
31. (b) Nicolaou, K.C.; Boddy, C.N.C.; Natarajan, S.; Yue, T.Y.; Li, H.; Brase, S.; Ramanjulu, J.M. J.Am.Chem.Soc. 1997, 119, 3421.
32. NAr see, for example: (a) Terrier, F. Nucleophilic Aromatic Displacement: The Role of the Nitro Group; VCH: New York, 1991, chapter 1;
33. (b) Artamkina, G.A.; Egorov, M.P.; Beletskaya, I.P. Chem.Rev. 1982, 82, 427.
34. (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;
35. (b) Kiselyov, A.S.; Armstrong, R.W. Tetrahedron Lett. 1997, 38, 6163;
36. (c) Kiselyov, A.S.; Eisenberg, S.; Luo, Y. Tetrahedron 1998, 54, 10635.
37. (a) Burgess, K.; Lim, D.; Bois-Choussy, M.; Zhu, J. Tetrahedron Lett. 1997, 38, 3345;
38. (b) Feng, Y.; Wang, Z.; Burgess, K. Books of Abstracts, 214th ACS National Meeting, Part 2, ACS, Houston, 1998, 054;
39. (c) Zhang, A.J.; Burgess, K. Books of Abstracts, 214th ACS National Meeting, Part 2, ACS, Houston, 1998, 246;
40. (d) Feng, Y.; Wang, Z.; Jin, S.; Burgess, K. J.Am.Chem.Soc. 1998, 120, 10768.
41. Bolin, D.R.; Sytwu, I.-I.; Humiec, F.; Meienhofer, J. Int.J.Pept. Protein Res. 1989, 33, 353.
42. Kamm, O.; Matthews, A.O. Org.Syn.Col. Vol. 1 1941, 392.
43. Ouyang, S.; Armstrong, R.W.; Murphy, M. J.Org.Chem. 1998, 63, 1027.
44. 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.
45. Carpino, L.A. J.Am.Chem.Soc. 1993, 115, 4397.