PL EN


Preferencje help
Widoczny [Schowaj] Abstrakt
Liczba wyników
Tytuł artykułu

Narzędzia chemii kombinatorycznej. Cz 3. Reakcje w syntezie organicznej na fazie stałej

Identyfikatory
Warianty tytułu
EN
Tools for combinatorial chemistry. Part 3. Reaction in solid phase organic synthesis
Języki publikacji
PL
Abstrakty
EN
Solid Phase Organic Synthesis (SPOS) is a dynamically growing branch of organic synthesis encompusing methods for synthesis of both small molecules and oligomers on solid supports. Synthetically useful organic reactions of substrates immobilized on solid supports constitute a central part of the methodology of solid phase synthesis. This review article presents a representative and fairly comprehensive overview of reactions of supported substrates published till January 2005. The reactions are classified in synthetic terms into functional group interconvertions (FG1, according to type of functional group reacting and prepared) and C-C bond forming reactions (according to reaction type; usually name reaction). Fn particular preparations of halogens, alcohols, ethers, thiols, aldehydes, ketones, acids, esters, amides, phosphines, amines, poliamines, peptides, peptoids, oligonucleotides, and oligosaccharides is covered. Oxidation reactions of alcohols, aldehydes and ketones as well as reduction reactions of aldehydes, ketones, esters, acids, nitro and nitroso compounds are also presented. Only the selected reactions used for preparation of oligonucleotides, oligosaccharides, and polypeptides are covered due to the large volume of literaturę on this topie. The important C-C bond forming reactions such as Mannich, Michael, aldol, Heck, Suzuki, Stille, Sonogashira, Wittig, Horner-Wad-sworth-Emmons, metathesis, carbonyl compound alkylation and acylation reactions are illustrated with examples. Moreover the multicomponent reactions such as Ugi reaction, Hantzsch reaction and Baylis-Hillman reaction are also included in the review. The literature review shows a spectrum of synthetic organic reactions which can be performed on the immobilized substrates and suggests that in principle every reaction could be performed on solid phase. Howeverthe literature review indicates that reactions of polar organometallic reagents, radical reactions, and enantioselective reactions of achiral immobilized substrates are rather rarely used in SPOS.
Rocznik
Strony
881--952
Opis fizyczny
Bibliogr. 287poz., schem., tab.
Twórcy
autor
  • Instytut Chemii, Uniwersytet w Białymstoku, ul. Hurtowa 1, 15-399 Białystok
  • Instytut Chemii, Uniwersytet w Białymstoku, ul. Hurtowa 1, 15-399 Białystok
  • Instytut Chemii, Uniwersytet w Białymstoku, ul. Hurtowa 1, 15-399 Białystok
Bibliografia
  • [1] R.B. Merrifield, J. Am. Chem. Soc., 1963, 85,2149.
  • [2] C.C. Leznoff, A cc. Chem. Ress., 1978,11,327.
  • [3] J.M. Frechet, Tetrahedron, 1981,37,663.
  • [4] Handbook of Combinatorial Chemistry, eds. K.C. Nicolaou, R. Hanko, W. Hartwig, Vol. 1-2, Wiley-VCH, Weinheim, 2002.
  • [5] P.H.H. Hermkens, H.C.J. Ottenheijm, D. Rees, Tetrahedron, 1996, 52,4527.
  • [6] P.H.H. Hermkens, H.C.J. Ottenheijm, D. Rees, Tetrahedron, 1997,53,5643.
  • [7] S. Booth, P.H.H. Hermkens, H.C.J. Ottenheijm, D. Rees, Tetrahedron, 1998, 54, 15385.
  • [8] S. Brase, J.H. Kirchhoff, J. Kobberling, Tetrahedron, 2003,59, 885.
  • [9] Combinatorial Chemistry, ed. H. Fenniri, Oxford University Press, Oxford, 2000.
  • [10] F.Z. Dorwald, Organic Synthesis on Solid Phase, Wiley-VCH, Weinheim, 2002.
  • [11] R.G. Franzen, J. Comb. Chem., 2000, 2, 195.
  • [12] V. Krchńak, M.W. Holladay, Chem. Rev„ 2002,102,61.
  • [13] S. Brase, C. Gil, K. Knepper, Bioorg. Med. Chem., 2002,10,2415.
  • [14] S. Brase, D. Enders, J. Kobberling, F. Avemaria, Angew. Chem. Int. Ed. Engl., 1998,37,3413.
  • [15] A. Ajayaghosh, V.N.R. Pillai, Tetrahedron, 1988,44, 6661.
  • [16] C.T. Bui, N.J. Maeji, F. Rasoul, A.M. Bray, Tetrahedron Lett., 1999,40, 5383.
  • [17] J.Y. Wong, C. Manning, C.C. Leznoff, Angew. Chem. Int. Ed. Engl., 1974,13,666.
  • [18] C.T. Bui, N.J. Maeji, A.M. Bray, Biotech. Bioeng. (Comb. Chem.), 2000, 71, 91.
  • [19] B. Raju, T.P. Kogan, Tetrahedron Lett., 1997,38,4965.
  • [20] Y. Han, A. Giroux, C. Lepine, F. Laliberte. Z. Huang, H. Perrier, C.I. Bayly, R.N. Young, Tetrahedron Lett., 1999,55, 11669.
  • [21] Y. Han, A. Roy, A. Giroux, Tetrahedron Lett., 2 000,41, 5447.
  • [22] K.A. Newlander, B. Chenera, D.F. Veber, N.C.F. Yim, M.L. Moore, J. Org. Chem., 1997.62,6726.
  • [23] K.C. Nicolaou, N. Winssinger, D. Vourloumis, T. Ohshima, S. Kim, J. Pfefferkom, Y.J. Xu, T. Li. J. Am. Chem. Soc., 1998,120,10814.
  • [24] M. Ramaseshan, Y.L. Dory, P. Deslongchamps, J. Comb. Chem., 2000, 2, 615.
  • [25] D.S. Brown, J.M. Revill, R.E. Shute, Tetrahedron Lett., 1998, 39, 8533.
  • [26] J.M J. Frechet, K.E. Haque, Tetrahedron Lett., 1975, 3055.
  • [27] H. Hayatsu, H.G. Khorana, J. Am. Chem. Soc., 1966, 88, 3182.
  • [28] H. Hayatsu, H.G. Khorana, J. Am. Chem. Soc., 1967. 89, 3880.
  • [29] D.A. Nugiel, D.A. Wacker, G.A. Nemeth, Tetrahedron Lett., 1997, 38, 5789.
  • [30] G.D. Darling, J.MJ. Frechet, J. Org. Chem., 1986, 51, 2270.
  • [31] C.A. Olsen, M. Witt, J.W. Jaroszewski, H. Franzyk, Org. Lett., 2004, 6, 1935.
  • [32] T. Zoller, J.-B. Ducep, M. Hibert, Tetrahedron Lett., 2000, 41, 9985.
  • [33] O. Mitsunobu, Synthesis, 1981,1.
  • [34] V. Krchnak, Z. Flegelova, A.S. Weichsel, M. Lebl, Tetrahedron Lett., 1995,36, 6193.
  • [35] T.A. Rano, K.T. Chapman, Tetrahedron Lett., 1995,36, 3789.
  • [36] L.M. Gayo, M.J. Suto, Tetrahedron Lett., 1997,38,211.
  • [37] V. Krchnak, A.S. Weichsel, M. Lebl, S. Felder, Bioorg. Med. Chem. Lett., 1997, 7. 1013.
  • [38] X. Du, R.W. Armstrong, J. Org. Chem., 1997, 62, 5678.
  • [39] S.M. Dankwardt, T.M. Phan, J.L. Krstenansky, Mol. Diversity, 1995, 1, 113.
  • [40] K.C. Nicolaou, N. Wissinger, J. Pastor, F. DeRoose, J. Am. Chem. Soc., 1997, 119,449.
  • [41] C.W. Phoon, C. Abell, J. Comb. Chem., 1999, 1, 485.
  • [42] D.R. Barn, J.R. Morphy, J. Comb. Chem., 1999,1, 151.
  • [43] J.M. Cobb, M.T. Fiorini, C.R. Goddard, M.E. Theoclitou, C. Abell, Tetrahedron Lett., 1999, 40, 1045.
  • [44] L.F. Tietze, A. Steinmetz, Synlett, 1996, 667.
  • [45] M. Barbaste, V. Rolland-Fulcrand, M.L. Roumestant, P. Viallefont, J. Martinez, Tetrahedron Lett., 1998,39,6287.
  • [46] P. Soucy, Y.L. Dory, P. Deslongchamps, Synlett, 2000, 1123.
  • [47] P. Karoyan, A. Triolo, R. Nannicini, D. Giannotti, M. Altamura, G. Chassaing, E. Perrotta, Tetrahedron Lett., 1999, 40,71.
  • [48] D.L. Whitehouse, S.N. Savinov, D.J. Austin, Tetrahedron Lett., 1997,38, 7851.
  • [49] D. Mormeneo, A. Llebaria, A. Delgado, Tetrahedron Lett., 2004, 45, 6831.
  • [50] R.N. Salvatore, F. Chu, A.S. Nagle, E.A. Kapxhiu, R.M. Cross, K.W. Jung, Tetrahedron, 2002 58, 3329.
  • [51] E.J. Moran, T.E. Wilson, C.Y. Cho, S.R. Cherry, P.G. Schultz, Biopolymers, 1995, 37, 213.
  • [52] K.C. Nicolaou, G.-Q. Cao, J.A. Pfefferkom, Angew. Chem. Int. Ed., 2000, 39, 739.
  • [53] P. Aiya, C.-Q. Wei, M.L. Bames, M. Doroszewska, J. Comb. Chem., 2004, 6, 65.
  • [54] A. Vidal-Ferran, N. Bampos, A. Moyano, M.A. Pericas, A. Riera, J.K.M. Sanders, J. Org. Chem., 1998,63, 6309.
  • [55] S.P. Hollinshead, Tetrahedron Lett., 1996,37, 9157.
  • [56] W.J. Haap, D. Kaiser, T.B. Walk, G. Jung, Tetrahedron, 1998, 54, 3705.
  • [57] K. Rolfing, M. Thiel, H. Kiinzer, Synlett, 1996, 1036.
  • [58] A.R. Katritzky, S.A. Belyakov, Y. Fang, J.S. Kiely, Tetrahedron Lett., 1998, 39, 8051.
  • [59] P.S. Furth, M.S. Reitman, A.F. Cook, Tetrahedron Lett., 1997,38, 5403.
  • [60] K.M. Brammond, J. Lu, J. Org. Chem. 1999, 64,1723.
  • [61] S. Brase, J. Kobberling, D. Enders, R. Lazny, M. Wang, S. Brandtner, Tetrahedron Lett., 1999,40, 2105.
  • [62] S. Kobayashi, Y. Aoki, Tetrahedron Lett., 1998,39,7345.
  • [63] S. Kobayashi, R. Akiyama, Tetrahedron Lett., 1998, 39,9211.
  • [64] R. Leger, R. Yen, M.W. She, V.J. Lee, S.J. Hecker. Tetrahedron Lett., 1998,39,4171.
  • [65] H.J. Kohlbau, J. Tschak.rt, R.A. Al-Qawasmeh, T.A. Niżami. A. Malik, W.Z. Voelter, Naturforsch. Sect. B, 1998. 53, 753.
  • [66] Lee, L. Huang, J.A. Ellman, J. Am. Chem. Soc., 1999,121. 9907.
  • [67] B.F. Gisin, Helv. Chim. Acta, 1973, 56, 1476.
  • [68] S. Yoo, S.J. Seo, K.Y. Yi, Y.D. Gong, Tetrahedron L ett.,1997,38. 1203.
  • [69] M.J. Kurth, L.A.A. Randall, C. Chen, C. Melander, R B. Miller, K. McAlister. G. Reitz, R Kang, T. Nakatsu, C. Green, J. Org. Chem., 1994,59, 5862.
  • [70] C. Gennari, S. Ceccarelli, U. Piarulli, K. Aboutayab, M. Donghi, I. Peterson, Tetrahedron. 1998, 54, 14999.
  • [71] R.S. Garigipati, Tetrahedron Lett., 1997,38,6807.
  • [72] F.M. Adrian, B. Altava, M.I. Burguete, S.V. Luis, R.V. Salvador, E. Garda-Espana, Tetrahedron, 1998, 54,3581.
  • [73] D.F.J. Sampson, R G. Simmonds, M. Bradley, Tetrahedron Lett., 2001,42,5517.
  • [74] H. Yuasa, Y. Kamata, S. Kurono, H. Hashimoto, Bioorg. Med. Chem. Lett., 1998,8,2139.
  • [75] R.N. Zuckermann, J.M. Kerr, S.B.H. Kent, W.H. Moos, J. Am. Chem. Soc., 1992,114,10646.
  • [76] S.-H.L. Chiu, L. Anderson, Carbohyd. Res., 1976, 50,227.
  • [77] M. Adamczyk, J.R. Fishpaugh, P.G. Mattingly, Tetrahedron Lett., 1999, 40,463.
  • [78] V. Bertini, F. Lucchesini, M. Pocci, A. De Munno, Tetrahedron Lett., 1998,39,9263.
  • [79] T. Masąuelin, N. Meunier, F. Gerber, G. Rossę, Heterocycles, 1998,48,2489.
  • [80] S. Kobayashi, I. Hachiya, S. Suzuki, M. Moriwaki, Tetrahedron Lett, 1996,37,2809.
  • [81] Barco, S. Benetti, C. De Risi, P. Marchetti, G.P. Pollini, V. Zanirato, Tetrahedron Lett., 1998,39, 7591.
  • [82] Mansour, M. Portnoy, J. Chem. Soc., Perkin 1, 2001, 952.
  • [83] P.W. Davis, T.A. Vickers, L. Wilson-Lingardo, J.R. Wyatt, C.J. Guinosso, Y.S. Sanghvi, E.A. DeBaets, O.L. Acevedo, P.D. Cook, D.J. Ecker, J. Med. Chem., 1995,38,4363.
  • [84] M .R Pavia, M.P. Cohen, G.J. Dilley, G.R. Dubuc, T.L. Durgin, F.W. Forman, M.E. Hediger, G. Milot, T.S. Powers, 1. Sucholeiki, S. Zhou, D.G. Hangauer, Bioorg. Med. Chem., 1996,4,659.
  • [85] A.M. Barber, LR. Hardcastle, M.G. Rowlands, B.P. Nutley, J.H. Marriott, M. Jarman, Bioorg. Med. Chem. Lett., 1999, 9, 623.
  • [86] Peyman, C. Weiser, E. Uhlmann, Bioorg. Med. Chem. Lett., 1995, 5,2469.
  • [87] X.B. Yang, A. Sierzchala, K. Misiura, W. Niewiarowski, M. Sochacki, W.J. Stec, M.W. Wieczorek, J. Org. Chem., 1998, 63, 7097.
  • [88] E.E. Swayze, Tetrahedron Lett., 1997, 38, 8643.
  • [89] C. Lee, E.K. Kick, J.A. Ellman, J. Am Chem. Soc., 1998, 120, 9735.
  • [90] K.C. Nicolaou, N. Winssinger, J. Pastor, S. Ninkovic, F. Sarabia, Y. He, D. Vourloumis, Z. Yang, T. Li, P. Giannakakou, E. Hamel, Nature, 1997,387,268
  • [91] J.A. Hunt, W.R. Roush, J. Am. Chem. Soc., 1996,118, 9998.
  • [92] W.K.-D. Brill, A. De Mesmaeker, S. Wendebom, Synlett, 1998, 1085.
  • [93] S. Wendebom, A. De Mesmaeker, W.K.D. Brill, Synlett, 1998, 865.
  • [94] B. Peschke, J.G. Bundgaard, J. Breinholt, Tetrahedron Lett., 2001,42, 5127.
  • [95] W.M. Bryan, W.F. Huffman, P.K. Bhatnagar, Tetrahedron Lett., 2000, 41,6997.
  • [96] S. Berteina, A. De Mesmaeker, S. Wendebom, Synlett, 1999, 1121.
  • [97] J.J.N. Veerman, J.H. van Maarseveen, G.M. Visser, C.G. Kruse, H.E. Schoemaker, H. Hiemstra, F.P.J.T. Rutjes, Eur. J. Org. Chem., 1998, 2583.
  • [98] K.C. Nicolaou, D. Vourloumis, T. Li, J. Pastor, N. Winssinger, Y. He, S. Ninkovic, F. Sarabia, H. Vallberg, F. Rohschangar. M.P. King, M.R.V. Finlay, R Giannakakou, P. Verdier-Pinard, E. Hamel, Angew. Chem. Int. Ed. Engl., 1997,36, 2097.
  • [99] M.A. Marx, A.-L. Grillot, C.T. Louer, K.A. Beaver, RA. Bartlett, J. Am. Chem. Soc., 1997, 119, 6153.
  • [100] B. Borhan, J.A. Wilson, M.J. Gasch, Y. Ko, D.M. Kurth, M.J. Kurth, J. Org. Chem., 1995, 60, 7375.
  • [101] A.M. Fivush, T.M. Willson, Tetrahedron Lett., 1997,38, 7151.
  • [102] D.P. Rotella, J. Am. Chem. Soc., 1996, 118, 12246.
  • [103] C. Chen, L.A.A. R andall, R.B. Miller, A.D. Jones, M.J. Kurth, J. Am. Chem. Soc., 1994,116,2661.
  • [104] U. Reiser, J. Jauch, Synlett, 2001, 90.
  • [105] K.C. Nicolaou, J. Pastor, N. Winssinger, F. Murphy, J. Am. Chem. Soc., 1998,120, 5132
  • [106] K.C. Nicolaou, RS. Baran, Y.-L. Zhong, J. Am. Chem. Soc., 2 0 0 0 ,122, 10246.
  • [107] A.M. Bray, D.S. Chiefari, R.M. Valerio, N.J. Maeji, Tetrahedron Lett., 19 9 5 ,3 6, 5081.
  • [108] P.C. Miller, T.J. Owen, J.M. Molyneaux, J.M. Curtis, C.R. Jones, J. Comb. Chem., 1999, 1, 223.
  • [109] C.C. Leznoff, T.M. Fyles, J. Weatherston, Can. J. Chem., 1977, 55, 1143.
  • [110] W.H. Pearson, R.B. Clark, Tetrahedron Lett., 1997,38, 7669.
  • [111] T.L. Boehm, H.D.H. Showalter, J. Org. Chem., 1996, 61, 6498.
  • [112] B. Yang, Q. Sun, J.R. Wareing, C.F. Jewell, J. Org. Chem., 1996, 61, 8765.
  • [113] W. Li, B. Yan, J. Org. Chem., 1998, 63,4092.
  • [114] C. Chen, L.A.A. Randall, B.R. Miller, A.D. Jones, M.J. Kurth, Tetrahedron, 1997, 53, 6595.
  • [115] M. Reggeelin, V. Brening, R. Welcker, Tetrahedron Lett., 1998, 39, 4801.
  • [116] C.L. Cavallaro, T. Herpin, B.F. McGuinness, Y.C. Shimshock, R.E. Dolle, Tetrahedron Lett., 1999, 40,2711.
  • [117] X. Beebe, N.E. Schore, M.J. Kurth, J. Am. Chem. Soc., 1992,114, 10061.
  • [118] A.R. Katritzky, D. Toader, K. Watson, J.S. Kiely, Tetrahedron Lett., 1997, 38, 7849.
  • [119] P.F. Alewood, R.I. Brinkworth, R.J. Dancer, B. Gamham, A. Jones, S.B.H. Kent, Tetrahedron Lett., 1992,33,977.
  • [120] A.V. Purandare, M.A. Poss, Tetrahedron Lett., 1998,39, 935.
  • [121] M.R. Pavia. H.V. Meyers, G. Milot, M.E. Hediger, US Patent No. WO 99/33431, July 8, 1999.
  • [122] P. Sieber, Tetrahedron Lett., 1987,28,2107.
  • [123] D.R. Cody, S.H.H. DeWitt, J.C. Hodges, J.S. Kiely, W.H. Moos, M.R. Pavia, B.R. Roth, M.C. Schroeder, C J. Stankovic, US Patent No. 5,324,483, June 28, 1994.
  • [124] RJH. Schlessinger, C.P. Bergstrom, Tetrahedron Lett., 1996, 37, 2133.
  • [125] B. Furman, R. Thurmer, Z. Kaluza, R. Lysek, W. Volter, M. Chmielewski, Angew. Chem. Int. Ed., 1999,38, 1121.
  • [126] S. Hanessian, F. Xie, Tetrahedron Lett., 1998,39, 737.
  • [127] S. Wang, J. Am. Chem. Soc., 1973, 95, 1328.
  • [128] R.S. Garigipati, B. Adams, J.L. Adams, S.K. Sarkar, J. Org. Chem., 1996, 61, 2911
  • [129] S. Chandrasekhar, M.B. Padmaja, Synth. Commun., 1998,28, 3715.
  • [130] A.S. KiseIyov, R.W. Amstrong, Tetrahedron Lett., 1997, 38, 6163.
  • [131] G.A. Morales, J.W. Corbett, W.F. DeGrado, J Org. Chem., 1998, 63, 1172.
  • [132] F. Zaragoza, H. Stephensen, J. Org. Chem., 1999, 64,2555.
  • [133] C.L. Lee, KP. Chan, Y. Lam, S.Y. Lee, Tetrahedron Lett., 20 0 1 ,4 2, 1167.
  • [134] J. Lee, W.V. Murray, R.A. Rivero, J. Org. Chem., 1997, 62, 3874.
  • [135] R.A. Scheuerman, D. Tumelty, Tetrahedron Lett., 2000, 41, 6531.
  • [136] A. Hari, B.L. Miller, Tetrahedron Lett., 1999, 40,245.
  • [137] A. Kamal, G.S.K. Reddy, K.L. Reddy, Tetrahedron Lett., 2001, 42, 6969.
  • [138] G.B. Phillips, G.P. Wei, Tetrahedron Lett., 1996,37,4887.
  • [139] I. Hughes, Tetrahedron Lett., 1996,37, 7595.
  • [140] R. Di Lucrezia, I.H. Gilbert, C.D. Floyd, J. Comb. Chem., 2000. 2.249.
  • [141] J.H. Kirchhoff, S. Brase, D. Enders, J. Comb. Chem., 2001,3. 71.
  • [142] D. Enders, J.H. Kirchhoff, J. Kobberling, T.H. Peiffer, Org. Lett., 2001. 3. 1241.
  • [143] R. Lazny, M. Michalak, Synlett, 2002, 1931.
  • [144] R. Lazny, A. Nodzewska, K. Wolosewicz, Synthesis. 2003, 2858.
  • [145] J.S. Panek, B. Zhu, J. Am. Chem. Soc., 1997,119, 12022.
  • [146] B.C. Hamper, S.A. Kołodziej, A.M. Scates, Tetrahedron Lett., 1998,39,2047.
  • [147] B.A. Lorsbach, J.T. Bagdanoff, R B. Miller, M.J. Kurth, J. Org. Chem., 1998, 63,2244.
  • [148] C.C. Leznoff, D.M. Dixit. Can. J. Chem., 1997,55,3351.
  • [149] E. Falb, T. Yechezkel, Y. Salitra, C. Gilon, i. Pep. Res., 1999, 53, 507.
  • [150] Z. Zhu, B. McKittrick, Tetrahedron Lett., 1998,39,7479.
  • [151] H.-G. Chao, M.S. Bernatowicz, P.D. Reiss, C.E. Klimas. G.R. Matsueda, J. Am. Chem. Soc., 1994, 116, 1746.
  • [152] J.A. Linn, S.W. Gerritz, A.L. Handlon, C.E. Hyman, D. Heyer, Tetrahedron Lett., 1999.40,2227.
  • [153] K. Gordon, M. Bolger, N. Khan, S. Balasubramanian, Tetrahedron Lett., 2000,41, 8621.
  • [154] B. Them, J. Rudolph, G. Jung, Tetrahedron Lett., 2002, 43, 5013.
  • [155] M. Bodanszky, Principles of Peptide Synthesis, Springer, Berlin 1993.
  • [156] N. Sewald, H.-D. Jakubke, Peptides: Chemistry and Biology, Wiley-VCH, Weinheim, 2002.
  • [157] D.L. Griffith, M.J. 0'DonnelI, R.S. Pottorf, W.L. Scott, J.A. Porco Jr., Tetrahedron Lett., 1997,38, 8821.
  • [158] S.-Y. Han, Y.-A. Kim, Tetrahedron, 2004, 60,2447.
  • [159] L.A. Carpino, H. Imazumi, A. El-Faham, F.J. Ferrer. C. Zhang, Y. Lee, B.M. Foxman, P. Henklein. C. Hanay, C. Miigge, H. Wenschuh, J. Klose, M. Beyermann, M. Bienert, Angew. Chem. Int. Ed., 2002 ,41 ,442.
  • [160] L.A. Carpino, J. Xia, C. Zhang, A. El-Faham, J. Org. Chem., 2004, 69,62.
  • [161] F. A lbericio, J.M. Bofill, A. El-Faham, S.A. Kates, J. Org. Chem., 1998, 63, 9678.
  • [162] A.R. Mitchell, B.W. Ericskon; M.N. Ryabtsev, R.S. Hodges, R.B. Merrifield, J. Am. Chem. Soc., 1976,98, 7357.
  • [163] J.A. Camarero, B.J. Hackel, J.J. de Yoreo, A.R. Mitchell, J. Org. Chem., 2004, 69, 4145.
  • [164] I. Clark-Lewis, R. Aebersold, H. Ziltener, J.W. Schrader, L.W. Hood, S.B.H. Kent, Science. 1986. 231, 134.
  • [165] Novabiochem Catalog and Peptide Synthesis Handbook, CH 1999.
  • [166] J. Jones, The Chemical Synthesis of Peptides, Oxford University Press, Oxford, 1994.
  • [167] G.B. Fields, R.L. Noble, Int. J. Pept. Prot. Res., 1990,35,161.
  • [168] N. Robertson, R. Ramage, J. Chem. Soc. Perkin 1,1999, 1015.
  • [169] H.S. Trivedi, M. Anson, P.G. Steel, J. Worley, Synlett, 2001, 1932.
  • [170] V. Lejeune, J. Martinez, F. Cavelier, Tetrahedron Lett., 2003, 44,4757.
  • [171] D.S. Wagner, C.J. Markworth, C.D. Wagner, F.J. Schoenen, C.E. Rewerts, B.K. Kay. H.M. Geysen, Comb. Chem. High Throughput Screening, 1998,1,143.
  • [172] H.J. 01ivos, P.G. Alluri, M.M. Reddy, D. Salony, T. Kodadek. Org. Lett, 2 0 02,4,4057.
  • [173] N. Heine, T. Ast, J. Schneider-Mergener, U. Reineke, L. Germeroth, H. Wenschuh, Tetrahedron. 2003, 59 ,9919.
  • [174] R.L. Letsinger, V. Mahadevan, J. Am. Chem. Soc., 1965, 87, 3526.
  • [175] K. Itakura, C.P. Bahl, N. Katagiri, J.J. Michniewicz, R.H. Wightman, S.A. Narang, Can. J. Chem., 1973, 51, 3649.
  • [176] H. Ito, Y. Ike, S. Itakura, Nucleic Acids Res., 1982, 10, 1755
  • [177] J.C. Catlin, F. Cramer, J. Org. Chem., 1973,38,245.
  • [178] M. Sekine, T. Hata, Curr. Org. Chem., 1 999,3,25.
  • [179] G.R. Gough, M.J. Brunden, P.T. Gilham, Tetrahedron Lett., 1981, 22, 4177.
  • [180] F. Eckstein, Oligonucleotides and Analogues, A Practical Approach, Oxford Uniwersity Press. Oxford, 1991.
  • [181] A.B. Sierzchala, D.J. Dellinger, J.R. Betley, T.K. Wyrzykiewicz, C.M. Yamada, M.H. Caruthers, J. Am. Chem. Soc., 2003 ,125, 13427.
  • [182] R. Micura, Chem. Eur. J., 1999, 5,2077.
  • [183] M. Frieden, A. Grandas, E. Pedroso, Chem. Commun., 1999, 1593.
  • [184] A. Ohkubo, K. Seio, M. Sekine, Tetrahedron Lett, 2004, 45, 363.
  • [185] D.J. Silva, H. Wang, MM. Allanson, R.K. Jain, M.J. Sofia, J. Org. Chem., 1999, 64, 5926.
  • [186] Y. Wang, H. Zhang, W, Voelter, Chem. Lett., 1995 273.
  • [187] L. Yan, C.M. Taylor, R. Goodnow, D. Kahne, J. Am. Chem. Soc., 1994,116, 6953.
  • [188] R. Liang, L. Yan, J. Loebach, M. Ge, Y. Uozumi, K. Sekanina, N. Horan, J. Gildersleeve, C. Tompson, A. Smith, K. Biswas, W.C. Still, D. Kahne, Science, 1996, 274, 1520.
  • [189] C. Zheng, P.H. Seeberger, S.J. Danishefsky, J. Org. Chem., 1998, 37, 1126.
  • [190] T. Zhu, G.-J. Boons, Angew. Chem. Int. Ed., 1998, 37, 1898.
  • [191] Y. Ito, O. Kanie, T. Ogawa., Angew. Chem. Int. Ed. Engl., 1996,35, 2510.
  • [192] X Wu, M. Grathwohl, R R. Schmidt, Angew. Chem. Int. Ed., 2002, 4 1 ,4 4 8 9.
  • [193] D. Jonsson, Tetrahedron Lett., 2002,43, 4793.
  • [194] D. Jonsson, A. Unden, Tetrahedron Lett., 2002,43, 3125.
  • [195] L.S. Richter, S. Andersen, Tetrahedron Lett., 1998, 39, 8747.
  • [196] H.-C. Zhang, K.K. Brumfield, L. Jaroskova, B.E. Maryanoff, Tetrahedron Lett., 1998, 39, 4449.
  • [197] M.A. Yougman, S.L. Dax, Tetrahedron Lett., 1997, 38,6347.
  • [198] J.J. McNally, M.A. Youngman, S.L. Dax, Tetrahedron Lett., 1998, 39, 967.
  • [199] S. Schunk, D. Enders, Org. Lett., 2001 ,3, 3177.
  • [200] E. Dominguez, M.J. O'Donnell, W.L. Scott, Tetrahedron Lett., 1998, 39, 2167.
  • [201] S. Kobayashi, R. Akiyama, T. Furuta, M. Moriwaki, Molecules Online, 1998, 2, 35.
  • [202] C. Chiu, Z. Tang, J.W. Ellingboe, J. Comb. Chem., 1999, 1, 73.
  • [203] Y. Wang, S.R. Wilson, Tetrahedron Lett., 1997,38, 4021.
  • [204] R. Lazny, A. Nodzewska, Tetrahedron Lett, 2003,44, 2441.
  • [205] T. Ruhland, L.A. Künzer, Tetrahedron Lett., 1996,37, 2757.
  • [206] S.P. Hollinshead, WO 98/08813.
  • [207] I. Paterson, M. Donghi, K. Gerlach, Angew. Chem. Int. Ed., 2000, 112, 3453.
  • [208] M. Reggelin, V. Brenig, Tetrahedron Lett., 1996,37, 6851.
  • [209] M. Reggelin, V. Brenig, C. Zur, Org. Lett., 2000, 2,531.
  • [210] S. Kobaysashi, I. Hachiya, M. Yasuda, Tetrahedron Lett., 1996,37, 5569.
  • [211] J. Tois, A. Koskinen, Tetrahedron Lett., 2003, 44,2093.
  • [212] R.G. Franzen, Tetrahedron, 2000,56, 685.
  • [213] S. Berteina, S. Wondebom, W.K.-D. Brill, A. De Mesmaeker, Synlett, 1998, 676.
  • [214] T.R. Early, R.S. Gordon, M.A. Caroll, A.B. Holmes, R.E. Shute, I.F. McConvey, Chem. Commun., 2001,1966.
  • [215] M. Hiroshige, J.R. Hauske, P. Zhou, Tetrahedron Lett., 1995,36, 4567.
  • [216] B. Ruhland, A. Bombrun, M.A. Gallop, J. Org. Chem., 1997, 62, 7820.
  • [217] K.-L. Yu, M.S. Deshpande, D.M. Vyas, Tetrahedron Lett., 1994, 35, 8919.
  • [218] M. Hiroshige, J.R. Hauske, P. Zhou, J. Am. Chem. Soc., 1995,117, 11590.
  • [219] K. Akaji, Y. Kisio, Tetrahedron Lett., 1997,38,5185.
  • [220] K. Akaji, K. Teruya, M. Akaji, S. Aimoto, Tetrahedron, 2001, 57, 2293.
  • [221] W.Y. Yun, R. Mohan, Tetrahedron Lett., 1996.37. 7189.
  • [222] H.C. Zhang, B.E. Maryanoff J. Org. Chem., 1997.62. 1804.
  • [223] R.N. Zuckermann, D.A. Goff, S. Ng, K. Spear. B.O. Scott. A. Sigmund, R.A. Goldsmith. C.K. Marlowe, Y. Pei, L. Richter, R. Simon (Chiron Corporation.). WO 96/40202. 1996.
  • [224] G.L. Bolton, J.C. Hodges, J. Com. Chem., 1999, 1, 130.
  • [225] S. Berteina, S. Wondebom, A. DeMesmaeker, Synlett. 1998, 1231.
  • [226] Suzuki, J. Organomet. Chem., 1999, 576,147.
  • [227] F.X. Woolard, J. Paetsch, J.A. Ellman, J. Org. Chem., 1997, 62,6102.
  • [228] Y. Lee, R.B. Silverman, Tetrahedron, 2001, 57,5339.
  • [229] S. Wendebom, S. Berteina, W.K.-D. Brill, A. De Mesmaeker. Synlett, 1998, 671.
  • [230] R.J. Kell, P. Hodge, M. Nisar. R.T. Williams, J. Chem. Soc., PerKin 1.2001, 3403.
  • [231] P.A. Tempest, R.W. Armsrtong, J. Am. Chem. Soc., 1997. 119, 7607.
  • [232] S.A. Ohnmacht, T. Brenstrum, K.H. Bleicher, J. McNuIty, A. Capretta, Tetrahedron Lett., 2004.45. 5661.
  • [233] M.S. Deshpande, Tetrahedron Lett., 1994,35. 5613.
  • [234] M. Larhed, G. Lindeberg, A. Hallberg, Tetrahedron Lett., 1996.37, 8219.
  • [235] S. Chamoin, S. Houldsworth, V. Snieckus, Tetrahedron Lett., 1998, 39, 4175.
  • [236] M.S. Brody, M.G. Finn, Tetrahedron Lett., 1999, 40,415.
  • [237] M.C. Fagnola, 1. Candiani, G. Visentin, W. Cabri, F. Zarini, N. Mongelli. A. Bedeschi, Tetrahedron Lett., 1997,38, 2307.
  • [238] M.D. Collini, J.W. Ellingboe, Tetrahedron Lett., 1997,38, 7963.
  • [239] D. Fancelli, M.C. Fagnola, D. Severino, A. Bedeschi, Tetrahedron Lett., 1997,38,2311.
  • [240] J.K. Young, J.C. Nelson, J.S. Moore, J. Am. Chem. Soc., 1994,116, 10841.
  • [241] J.C. Nelson, J.K. Young, J.S. Moore, J. Org. Chem., 1996, 61. 8160.
  • [242] S. Brase, S. Dahmen, J. Heuts, Tetrahedron Lett., 1999,40, 6201.
  • [243] Y. Liao, R. Fathi, M. Reitman, Y. Zhang, Z. Yang, Tetrahedron Lett., 2001, 42,1815.
  • [244] M. Erdelyi, A. Gogoll, J. Org. Chem., 2003, 68, 6431.
  • [245] C.C. Leznoff, J.Y. Wong, Can. J. Chem., 1973, 51, 3756.
  • [246] U. Gerigk, M. Gerlach, W.P. Neumann, R. Vieler, V. Weintritt. Synthesis, 1990. 448.
  • [247] A.L. Marzinzik, E.R. Felder, J. Org. Chem., 1998,63,723.
  • [248] T. Doi, I. Hijikuro, T. Takahashi, J. Am. Chem. Soc., 1999, 121, 6749.
  • [249] J.M. Salvino, S. Kieslow, R. Dambrough, R. Labaudiniere, J. Comb. Chem., 1999. 1, 134.
  • [250] J.K. Bang, K. Hasegawa, T. Kawakami, S. Aimoto, K. Akaji, Tetrahedron Lett., 2004, 45, 99.
  • [251] D.A. Heerding, D.T. Takata, C. Kwon, W.F. Huffman, J. Samenen, Tetrahedron Lett., 1998, 39, 6815.
  • [252] J. Pemerstorfer, M. Schuster, S. Blechert, Synthesis, 1999, 138.
  • [253] M. Schuster, J. Pemerstorfer, S. Blechert, Angew. Chem. Int. Ed., 1996, 35, 1979.
  • [254] V. Chaleix, V. Sol, M. Guilloton, R. Granet, P. Krausz, Tetrahedron Lett., 2004,45, 5295.
  • [255] A.G.M. Barrett, A J. Hennessy, R. Le Vezouet, P.A. Procopiou, P.W. Seale, S. Stefaniak, R.J. Upton, A.J.P. White, D.J. Wiliams, J. Org. Chem., 2004, 69, 1028.
  • [256] G.D. Cuny, J. Cao, J.R. Hauske, Tetrahedron Lett., 1997,38,5237.
  • [257] G.D. Cuny, J. Cao, J.R. Hauske, Mol. Diversity, 1998,3, 173.
  • [258] G.D. Cuny, J. Cao, A. Sidhu, J.R. Hauske, Tetrahedron, 1999, 55, 8169.
  • [259] S.C.G. Biagini, S.E. Gibbon, S.P. Keen, J. Chem. Soc. Perkin 1, 1998, 2485.
  • [260] R. Lazny, A. Nodzewska, M. Sienkiewicz, K. Wolosewicz, J. Comb. Chem., 2005, 7, 109.
  • [261] A.L. Marzinzik, E.R. Felder, Tetrahedron Lett., 1996,37, 1003.
  • [262] S. Hanessian, J. Ma, W. Wang, Tetrahedron Lett., 1999,40, 4631.
  • [263] M.J. 0 ’Donnell, C.W. Lugar, R.S. Pottorf, C. Zhou. W.L. Scott, C.L. Cwi, Tetrahedron Lett., 1997, 38,7163.
  • [264] M.J. O’Donnell, C. Zhou, W.L. Scott, J. Am. Chem. Soc., 1996,118, 6070.
  • [265] H. Moon, N.E. Schore, M.J. Kurth, Tetrahedron Lett., 1994, 35, 8915.
  • [266] M.J. 0'Donnell, J. Alsina, W.L. Scott, Tetrahedron Lett., 2003, 44, 8403.
  • [267] Q. Ren, W. Huang, P. Ho, Reactive Polymers, 1989, 11,237.
  • [268] F. Bevacqua, A. Basso, R. Gitto, M. Bradley, A. Chimirri, Tetrahedron Lett., 2001, 42, 7683.
  • [269] J. Yli-Kuahaluoma, Tetrahedron, 2001, 57,7053.
  • [270] B.R. Stranix, G.D. Darling, J. Org. Chem., 1997, 62, 9001.
  • [271] V. Yedidia, C.C. Leznoff, Can. J. Chem., 1980, 58, 1144.
  • [272] J.D. Winkler, W. McCoull, Tetrahedron Lett., 1998, 3 9,4935.
  • [273] J. Barluenga, C. Mateos, F. Aznar, C. Valdes, Org. Lett, 2002, 4, 3667.
  • [274] A. Kiriazis, T. Leikoski, I. Mutikainen. J. Yli-Kauhaluoma, J. Comb. Chem., 2004, 6, 283.
  • [275] D. Brohm, N. Philippe, S. Metzger, A. Bhargava, O. Muller, F. Lieb, H. Waldmann, J. Am. Chem. Soc., 2002, 124, 13171.
  • [276] P. Lan, D. Berta, J.A. Porco, Jr, M.S. South, J.J. Parlow, J. Org. Chem., 2003, 68, 9678.
  • [277] N. Kaval, J. Van der Eycken, J. Caroen, W. Dehaen, G.A. Strohmeier, C.O. Kappe, E. Van der Eycken, J. Comb. Chem., 2003, 5, 560.
  • [278] D.V. Patel, M.F. Gordeev, B.P. England, E.M. Gordon, Mol. Diversity Combin. Chem: Lib. Drug Discovery, 1996, 58.
  • [279] M.F. Gordeev, D.V. Patel, B.P. England, S. Joannalagadda, J.D. Combs, E.M. Gordon, Bioorg. Med. Chem., 1998, 6, 883.
  • [280] H. Richter, G. Jung, Tetrahedron Lett., 1998, 3,2729.
  • [281] A.M. Strocker, T.A. Keating, P.A. Tempest, R.W. Armstrong, Tetrahedron Lett., 1996, 37, 1149.
  • [282] A.M.M. Mjalli, S. Sarshar, T.J. Baiga, Tetrahedron Lett., 1996,37, 2943.
  • [283] C. Zhang, E J. Moran, T.F. Woiwode, K.M. Short, A.M.M. Mjalli, Tetrahedron Lett., 1996,37,751.
  • [284] K.M. Short, A.M.M. Mjalli, Tetrahedron Lett., 1997, 38, 359.
  • [285] A.M.L. Hoel, J. Nielsen, Tetrahedron Lett, 1999,40, 3941.
  • [286] K.M. Short, B.W. Ching, A.M.M. Mjalli, Tetrahedron Lett., 1996,37, 7489
  • [287] A.K. Szardenings, T.S. Burkoth, H.H. Lu, D.W. Hen, D.A. Campbell, Tetrahedron, 1997,53,6573.
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BUS2-0009-0001
JavaScript jest wyłączony w Twojej przeglądarce internetowej. Włącz go, a następnie odśwież stronę, aby móc w pełni z niej korzystać.