Polymer supported synthesis of a natural product-inspired oxepane library

Bioorganic and Medicinal Chemistry

Volumn 22, Issue 16, 2014, Pages 4430-4444

  Basu, Sudipta ^a   Waldmann, Herbert ^a  

^a TU DORTMUND UNIVERSITY   (Germany)

Author keywords

Cross metathesis reaction; Cycloaddition; Enyne ring closing reaction; Immobilized scavengers; One pot synthesis; Oxepane; Polymer supported synthesis

Indexed keywords

2 FLUOROBENZOYL CHLORIDE; 2,4 DIMETHOXY PHENYL ISOCYANATE; 3,4 DICHLOROBENZOYL CHLORIDE; ALDEHYDE DERIVATIVE; ALIPHATIC ACID CHLORIDE DERIVATIVE; ALPHA BROMO ETHYL ACETATE DERIVATIVE; AROMATIC ACID CHLORIDE DERIVATIVE; BENZOQUINONE DERIVATIVE; CARBAMIC ACID DERIVATIVE; CHLOROPHENYL ISOCYANATE; DIEMTHYL ACETYLENE DIACARBOXYLATE; DIENENOPHILE DERIVATIVE; DIMETHYL ACETYLENE DICARBOXYLATE; ESTER DERIVATIVE; KETONE DERIVATIVE; MALEIC ANHYDRIDE; MALEIMIDE; METHYLBENZOYL CHLORIDE DERIVATIVE; N PHENYLMALEIMIDE; NAPHTHALENE; NATURAL PRODUCT; OXEPANE DERIVATIVE; OXIME DERIVATIVE; PHENYL ISOCYANATE; POLYMER; PROPARGYL ALCOHOL; PROPARGYL ALCOHOL DERIVATIVE; PYRIDINIUM CHLOROCHROMATE; SULFONIC ACID RESIN; UNCLASSIFIED DRUG; UNINDEXED DRUG; BIOLOGICAL PRODUCT; HETEROCYCLIC COMPOUND; MOLECULAR LIBRARY;

ARTICLE; BIOLOGICAL ACTIVITY; CATION EXCHANGE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; NONHUMAN; PROTON RADIATION; SYNTHESIS; CHEMISTRY; CONFORMATION; MOLECULAR LIBRARY;

BIOLOGICAL PRODUCTS; HETEROCYCLIC COMPOUNDS; MOLECULAR CONFORMATION; POLYMERS; SMALL MOLECULE LIBRARIES;

EID: 84906260305     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2014.05.039     Document Type: Article

References (46)

1. R. Breinbauer, I. Vetter, and H. Waldmann Angew. Chem., Int. Ed. 41 2002 2878
2. K. Kumar, and H. Waldmann Angew. Chem., Int. Ed. 48 2009 3224
3. M. Kaiser, S. Wetzel, K. Kumar, and H. Waldmann Cell. Mol. Life Sci. 65 2008 1186
4. S.V. Ley, and I.R. Baxendale Nat. Rev. Drug Disc. 1 2002 573 and the references therein
5. F.A. Macías, J.M.G. Molinillo, R.M. Varela, and A. Torres J. Org. Chem. 59 1994 8261
6. C.F.-L. Bon, F. Berrué, O.P. Thomas, F. Reyes, and P. Amade J. Nat. Prod. 68 2005 1284
7. A. Rudi, I. Goldberg, Z. Stein, and Y. Kashman J. Nat. Prod. 58 1995 1702
8. G. Guella, I. Mancini, G. Chiasera, and F. Pietra Helv. Chim. Acta 75 1992 310
9. S.D. Levine, R.E. Adams, R. Chen, M.L. Cotter, A.F. Hirsch, V.V. Kane, R.M. Kanijoa, C.J. Shaw, M.P. Wachter, E. Chin, R. Huetteman, P. Ostrowski, J.L. Mateos, L. Noriega, A. Guzmán, A. Mijarez, and L. Tovar J. Am. Chem. Soc. 101 1979 3404
10. G.B. Marcelle, N. Bunyapraphatsara, G.A. Cordell, H.S. Fong, K.C. Nicolaou, and R.E. Zipkin J. Nat. Prod. 48 1985 739
11. R.M. Kanojia, E. Chin, C. Smith, R. Chen, D. Rowand, S.D. Levine, M.P. Wachter, R.E. Adams, and D.W. Hahn J. Med. Chem. 28 1985 796
12. S. Wetzel, R.S. Bon, K. Kumar, and H. Waldmann Angew. Chem., Int. Ed. 50 2011 10800
13. R.S. Bon, and H. Waldmann Acc. Chem. Res. 43 2010 1103
14. A. Nören-Müller, I. Reis-Correa, H. Prinz, C. Rosenbaum, K. Saxena, H.J. Schwalbe, D. Vestweber, G. Cagna, S. Schunk, O. Schwarz, H. Schiewe, and H. Waldmann Proc. Natl. Acad. Sci. U.S.A. 103 2006 10606
15. A. Nören-Müller, W. Wilk, K. Saxena, H. Schwalbe, M. Kaiser, and H. Waldmann Angew. Chem., Int. Ed. 47 2008 5973
16. H. Waldmann, V. Khedkar, H. Dückert, M. Schürmann, I.M. Oppel, and K. Kumar Angew. Chem., Int. Ed. 47 2008 6869
17. A.P. Antonchick, C. Gerding-Reimers, M. Catarinella, M. Schurmann, H. Preut, S. Ziegler, D. Rauh, and H. Waldmann Nat. Chem. 2 2010 735
18. S. Basu, B. Ellinger, S. Rizzo, C. Deraeve, M. Schurmann, H. Preut, H.D. Arndt, and H. Waldmann Proc. Natl. Acad. Sci. U.S.A. 108 2011 6805
19. H. Dueckert, V. Pries, V. Khedkar, S. Menninger, H. Bruss, A.W. Bird, Z. Maliga, A. Brockmeyer, P. Janning, A. Hyman, S. Grimme, M. Schurmann, H. Preut, K. Hubel, S. Ziegler, K. Kumar, and H. Waldmann Nat. Chem. Biol. 8 2012 179
20. M. Potowski, J.O. Bauer, C. Strohmann, A.P. Antonchick, and H. Waldmann Angew. Chem., Int. Ed. 51 2012 9512
21. M. Potowski, M. Schurmann, H. Preut, A.P. Antonchick, and H. Waldmann Nat. Chem. Biol. 8 2012 428
22. B. Over, S. Wetzel, C. Grütter, Y. Nakai, S. Renner, D. Rauh, and H. Waldmann Nat. Chem. 5 2013 21
23. P.-Y. Dakas, J.A. Parga, S. Höing, H.R. Schöler, J. Sterneckert, K. Kumar, and H. Waldmann Angew. Chem., Int. Ed. 52 2013 9576
24. T. Voigt, C. Gerding-Reimers, T.N.T. Tuyen, S. Bergmann, H. Lachance, B. Scholermann, A. Brockmeyer, P. Janning, S. Ziegler, and H. Waldmann Angew. Chem., Int. Ed. 52 2013 410
25. A.P. Antonchick, S. López-Tosco, J. Parga, S. Sievers, M. Schürmann, H. Preut, S. Höing, H.R. Schöler, J. Sterneckert, D. Rauh, and H. Waldmann Chem. Biol. 20 2013 500
26. M. Potowski, A.P. Antonchick, and H. Waldmann Chem. Commun. 2013 7800
27. H. Takayama, Z.-J. Jia, L. Kremer, J.O. Bauer, C. Strohmann, S. Ziegler, A. Antonchick, and H. Waldmann Angew. Chem., Int. Ed. 52 2013 12404
28. R. Narajan, J.O. Bauer, C. Strohmann, A. Antonchick, and H. Waldmann Angew. Chem., Int. Ed. 52 2013 12892
29. V. Eschenbrenner-Lux, P. Kuechler, S. Ziegler, K. Kumar, and H. Waldmann Angew. Chem., Int. Ed. 53 2014 2134
30. M. Moreno-Mañas, R. Pleixats, and A. Santamaria Synlett 2001 1784
31. K.C. Majumdar, H. Rahaman, S. Muhuri, and B. Roy Synlett 2006 466
32. M.T. Crimmins, and A.C. DeBaillie Org. Lett. 5 2003 3009
33. P.K. Jadav, K.S. Bhat, T. Perumal, and H.C. Brown J. Org. Chem. 51 1986 432
34. R.I. Storer, T. Takemoto, P.S. Jackson, D.S. Brown, I.R. Baxendale, and S.V. Ley Chem. Eur. J. 10 2004 2529
35. M. Ahmed, A.G.M. Barrett, D.C. Braddock, S.M. Cramp, and R.A. Procopiou Tetrahedron Lett. 40 1999 8657
36. M. Westhus, E. Gonthier, D. Brohm, and R. Breinbauer Tetrahedron Lett. 45 2004 3141
37. N.K. Chadha, A.D. Batcho, P.C. Tang, L.F. Courtney, C.M. Cook, P.M. Wovkulich, and M.R. Uskoković J. Org. Chem. 56 1991 4714
38. M. Cano, M. Ladlow, and S. Balasubramanian J. Org. Chem. 67 2002 129
39. W.W. Harding, K. Tidgewell, N. Byrd, H. Cobb, C.M. Dersch, E.R. Butelman, R.B. Rothman, and T.E. Prisinzano J. Med. Chem. 48 2005 4765
40. A.B.I.I.I. Smith, P.V. Rucker, I. Brouard, B.S. Freeze, S. Xia, and S.B. Horwitz Org. Lett. 7 2005 5199
41. K.C. Nicolaou, S.A. Snyder, T. Montagnon, and G. Vassilikogiannakis Angew. Chem., Int. Ed. 41 2002 1668
42. A.K. Chatterjee, J.P. Morgan, M. Scholl, and R.H. Grubbs J. Am. Chem. Soc. 122 2000 3782
43. S.B. Garber, J.S. Kingsbury, B.L. Gray, and A.H. Hoveyda J. Am. Chem. Soc. 122 2000 8168
44. B.A. Kulkarni, G.P. Roth, E. Lobkovsky, and J.A. Porco Jr. J. Comb. Chem. 4 2002 56
45. H.E. Pelish, N.J. Westwood, Y. Feng, T. Kirchhausen, and M.D. Shair J. Am. Chem. Soc. 123 2001 6740
46. D.L. Boger, C.M. Tarby, P.L. Myers, and L.H. Caporale J. Am. Chem. Soc. 118 1996 2109