Zastosowanie glikali w syntezie glikopiranoz i glikopiranozydów

Liberek, B.

Artykuł - szczegóły

Tytuł artykułu

Zastosowanie glikali w syntezie glikopiranoz i glikopiranozydów

Autorzy

Liberek B.

Wybrane pełne teksty z tego czasopisma

Identyfikatory

Warianty tytułu

Application of glycals in the synthesis of glycopyranoses and glycopyranosides

Języki publikacji

Abstrakty

Glycals, systematically named l,5-(or 1,4-)anhydro-2-deoxy-hex-(or -pent-)l--enitols, posses a double bond between C-l and C-2 carbon atoms of a pyranose or furanose ring and are one of the most useful substrates in carbohydrate chemistry. Presence of the double bond in glycals makes them possible to undergo variety of the reactions, including different additions, hydroxylation, epoxydation, cycloadditions, allylic rearrangement and many others. The majority of these reactions were described in 1960s and 1980s by Ferrier. However, applications of glycals, especially as glycosyl donors, have been systematically developed and new methodologies have been employed in the last decade. This paper presents useful procedures, mainly resulting in the stereoselective synthesis of a glycoside bond. The presented applications of glycals are divided into following groups: addition of water, synthesis of 2-deoxyglycosides, synthesis of 2-amino--2-deoxyglycosides, synthesis of glycosides possessing 2-hydroxy group, Ferrier rearrangement, formation ofthe [alfa,beta]-unsaturated aldehydes, cyclopropanation and cycloaddition.

Słowa kluczowe

glikal addycja elektrofilowa 2-deoksygIikozyd 2-amino-2-deoksyglikozyd epoksydowanie przegrupowanie Ferriera alfa,beta-nienasycony aldehyd α,β-nienasycony aldehyd cyklopropanowanie cykloaddycja

glycal electrophilic addition 2-deoxyglycoside 2-amino-2-deoxyglycoside epoxydation Ferrier rearrangement alpha,beta-unsaturated aldehyde α,β-unsaturated aldehyde cyclopropanation cycloaddition

Wydawca

Polskie Towarzystwo Chemiczne

Czasopismo

Wiadomości Chemiczne

Rocznik

2006

Tom

[Z] 60, 7-8

Strony

487--521

Opis fizyczny

wykr., bibliogr. 181 poz.

Twórcy

autor

Liberek B.

Wydział Chemii, Uniwersytet Gdański, ul. J. Sobieskiego 18, 80-952 Gdańsk, beatal@chem. univ.gda.pl

Bibliografia

[1] T. Sokołowska, A. Wiśniewski, Nomenklatura Węglowodanów, Zalecenia 1996, Wydawnictwo Uniwersytetu Wrocławskiego, Wrocław 2000, 66.
[2] E. Fischer, K. Zach, Sitzber. Kgl. Preuss Akad.Wiss., 1913, 16, 311.
[3] W. Priebe, G. Grynkiewicz, [w:] Glycoscience: Chemistry and Chemical Biology, B. Fraser-Reid, K. Tatsuta, J. Thiem, Eds., Springer, Heidelberg, 2001, 749.
[4] J. Thiem, P. Ossowski, J. Carbohydr. Chem., 1984, 3, 287.
[5] R.J. Ferrier, Adv. in Carbohydr. Chem., 1965, 20, 68.
[6] R.J. Ferrier, [w:] The Carbohydrates, Chemistry and Biochemistry, W. Pigman, D. Horton, J.D. Wander, Eds., Academic Press: New York, 1980, Vol. IB, 843.
[7] E. Bettelli, P. Cherubini, P. D.Andrea, P. Passacantilli, G. Piancatelli, Tetrahedron, 1998, 54, 6011.
[8] A. Graziani, P. Passacantilli, G. Piancatelli, S. Tani, Tetrahedron: Asymmetry, 2000, 11, 3921.
[9] V. Costantino, C. Imperatore, E. Fattorusso, A. Mangoni, Tetrahedron Lett., 2000, 41, 9177.
[10] A.R. De Corso, B. Panunzi, M. Tingoli, Tetrahedron Lett., 2001, 42, 7245.
[11] R. Murali, M. Nagarajan, Carbohydr. Res., 1996, 280, 351.
[12] V. Bolitt, C. Mioskowski, S.-G. Lee, J.R. Falck, J. Org. Chem., 1990, 55, 5812.
[13] C.H. Marzabadi, R.W. Franck, Tetrahedron, 2000, 56, 8385.
[14] D.J. Wardrop,W. Zhang, Tetrahedron Lett., 2002, 43, 5389.
[15] S.J. Danishefsky, R.L. Halcomb, J. Am. Chem. Soc., 1991, 113, 5080.
[16] N. Kaila, M. Blumenstein, H. Bielawska, R.W. Franck, J. Org. Chem., 1992, 57, 4576.
[17] N. Kaila, H.-A. Yu, Y.B. Xiang, Tetrahedron Lett., 1995, 36, 5503.
[18] K.C. Nicolaou, J.I. Trujillo, K. Chibale, Tetrahedron, 1997, 53, 8751.
[19] S. Sebesan, S. Neira, J. Org. Chem., 1991, 56, 5468.
[20] O.B. Flekhter, L.A. Baltina, G.A. Tllstikov, Russ. Chem. Bull., 1997, 46, 1335.
[21] O.B. Flekhter, L.A. Baltina, L.V. Spirikhin, I.P. Baikhova, G.A. Tolstikov, Russ. Chem. Bull., 1998, 47, 513.
[22] D.P. Curran, R. Ferritto, Y. Hua, Tetrahedron Lett., 1998, 39, 4937.
[23] R.G. Dushin, S.J. Danishefsky, J. Am. Chem. Soc., 1992, 114, 3471.
[24] C. Mouton, F. Tillequin, E. Seguin, C. Monneret, J. Chem. Soc., Perkin Trans. 1, 1998, 2055.
[25] C. Booma, K.K. Balasubramanian, Tetrahedron Lett., 1995, 36, 5807.
[26] K. Toshima, H. Nagai, Y. Ushiki, S. Matsumara, Synlett, 1998, 1007.
[27] J.S.Yadav, B.V.S. Reddy, K. Bhaskar Reddy,M. Satyanarayana,Tetrahedron. Lett., 2002,43, 7009.
[28] K. Takiura, S. Honda, Carbohydr. Res., 1972, 21, 379.
[29] R.U. Lemieux, A.R. Morgan, Can. J. Chem., 1965, 43, 2190.
[30] H. Paulsen, M. Springer, F. Reck, I. Brockhausen, H. Schachter, Carbohydr. Res., 1995, 275, 403.
[31] Y. Ogawa, H. Hinou, K. Matsuoka, D. Terunuma, H. Juzuhara, Tetrahedron Lett., 1998, 39, 5789.
[32] M. Izumi, Y. Ichikawa, Tetrahedron Lett., 1998, 39, 2079.
[33] K. Suzuki, G.A. Sulikowski, R.W. Friesen, S.J. Danishefsy, J. Am. Chem. Soc., 1990, 112, 8895.
[34] R.W. Friesen, S.J. Danishefsky, J. Am. Chem. Soc., 1989, 111, 6656.
[35] R.W. Friesen, S.J. Danishefsky, Tetrahedron, 1990, 46, 103.
[36] D.B. Berkowitz, S.J. Danishefsky, G.K. Schulte, J. Am. Chem. Soc., 1992, 114, 4518.
[37] S.J. Danishefsky, M.T. Bilodeau, Angew. Chem. Int. Ed. Engl., 1996, 35, 1380.
[38] J. Thiem, H. Karl, J. Schwentner, Synthesis, 1978, 696.
[39] J. Thiem, H. Karl, Tetrahedron Lett., 1978, 50, 4999.
[40] J. Thiem,W. Klaffke, J. Org. Chem., 1989, 54, 2006.
[41] J. Thiem, S. Köpper, Tetrahedron, 1990, 46, 113.
[42] S. Köpper, J. Thiem, Carbohydrate Res., 1994, 260, 219.
[43] S. Köpper, D. Springer, J. Thiem, J. Carbohydr. Chem., 1994, 13, 1065.
[44] D. Horton, W. Priebe, Carbohydr. Res., 1985, 136, 391.
[45] D. Horton, W. Priebe, O. Varela, Carbohydr. Res., 1984, 130, C1.
[46] D. Horton, W. Priebe, M. Sznaidman, Carbohydr. Res., 1990, 205, 71.
[47] S. Oscarson, U. Tedebark, Carbohydr. Res., 1995, 278, 271.
[48] H.M.R. Hoffmann, U. Herden, M. Breithor, O. Rhode, Tetrahedron, 1997, 53, 8383.
[49] S.W.T. Choe, M.E. Jung, Carbohydr. Res., 2000, 329, 731.
[50] R.W. Friesen, S.J. Danishefsky, Tetrahedron, 1990, 46, 103.
[51] D. Lafont, P. Boullanger, F. Carvalho, P. Vottero, Carbohydr. Res., 1997, 297, 117.
[52] D. Lafont, P. Boullanger, M. Rosenzweig, J. Carbohydr. Chem., 1998, 17, 1377.
[53] W.R. Roush, S. Narayan, C.E. Bennett, K. Briner, Org. Lett., 1999, 1, 895.
[54] W.R. Roush, S. Narayan, Org. Lett., 1999, 1, 899.
[55] W.R. Roush, C.E. Bennett, J. Am Chem. Soc., 1999, 121, 3541.
[56] P.Y. Chong, W.R. Roush, Org. Lett., 2002, 4, 4523.
[57] T.B. Durham, W.R. Roush, Org. Lett., 2003, 5, 1871.
[58] W.R. Roush, R.A. Hartz, D.J. Gustin, J. Am. Chem. Soc., 1999, 121, 1990.
[59] M. Arai, S. Kaneko, T. Konosu, Tetrahedron Lett., 2002, 43, 6705.
[60] D.G. Gammon, H.H. Kinfe, D.E. De Vos, P.A. Jacobs, B.F. Sels, Tetrahedron Lett., 2004, 45, 9533.
[61] A. Kirschning, M. Jesberger, H. Monenschein, Tetrahedron Lett., 1999, 40, 8999.
[62] K. Dax, M. Albert, J. Ortner, B.J. Paul, Carbohydr. Res., 2000, 327, 47.
[63] J.D. McCarter, M.J. Adam, C. Braun, M. Namchuk, D. Tull, S.G. Withers, Carbohydr. Res., 1993, 249, 77.
[64] C.C. Geilen, N. Loch, W. Reutter, K. Seppelt, F. Oberdorfer, Tetrahedron Lett., 1992, 33, 2435.
[65] M.D. Burkart, Z. Zhang, S.-C. Hung, C.-H. Wong, J. Am. Chem. Soc., 1997, 119, 11743.
[66] S.P. Vincent, M.D. Burkart, C.-Y. Tsai, Z. Zhang, C.-H. Wong, J. Org. Chem., 1999, 64, 5264.
[67] M. Albert, K. Dax, J. Ortner, Tetrahedron, 1998, 54, 4839.
[68] Y. Ito, T. Ogawa, Tetrahedron Lett., 1987, 28, 2723.
[69] G. Grewal, N. Kaila, R.W. Franck J. Org. Chem., 1992, 57, 2084.
[70] S. Hashimoto, Y. Yanagiya, T. Honda, S. Ikegami, Chem. Lett., 1992, 1511.
[71] W.R. Roush, D.P. Sebesta, R.A. James, Tetrahedron, 1997, 53, 8837.
[72] D.P. Sebesta,W.R. Roush, J. Org. Chem., 1992, 57, 4799.
[73] M. Perez, J.-M. Beau, Tetrahedron Lett., 1989, 30, 75.
[74] K.C. Nicolaou, J. Pastor, S. Barluenga, N. Winssinger, Chem. Commun., 1998, 1947.
[75] J. Borowiecka, P. Lipka, M. Michalska Tetrahedron, 1988, 44, 2067.
[76] H. Bielawska, M. Michalska Tetrahedron Lett., 1998, 39, 9761.
[77] P. Somak, J. Narayanaswamy Carbohydr. Res., 2004, 339, 2197.
[78] J. Banoub, P. Boullanger, D. Lafont, Chem. Rev., 1992, 92, 1167.
[79] P.M. Collins, R.J. Ferrier, Monosaccharides, Their Chemistry and Their Roles in Natural Products, J. Wiley & Sons, Chichester, 1995, 217.
[80] R.U. Lemieux, T.L. Nagabhushan, S.W. Gunner, Can. J. Chem., 1968, 46, 405.
[81] B. Liberek, Z. Smiatacz, Wiad. Chem., 1999, 53, 461.
[82] A. Banaszek, W. Karpiesiuk, Carbohydr. Res., 1994, 251, 233.
[83] B. Liberek, R. Frankowski, Z. Smiatacz, Polish J. Chem., 1999, 73, 1153.
[84] R.U. Lemieux, R.M. Ratcliffe, Can. J. Chem., 1979, 57, 1244.
[85] W. Kinzy, R.R. Schmidt, Tetrahedron Lett., 1987, 28, 1981.
[86] P.H. Seeberger, S. Roehring, P. Schell, Y. Wang,W.J. Christ, Carbohydr. Res., 2000, 328, 61.
[87] J.B. Schwarz, S.D. Kuduk, X.-T. Chen, D. Sames, P.W. Glunz, S.J. Danishefsky, J. Am. Chem. Soc., 1999, 121, 2662.
[88] H. Herzner, T. Reipen, M. Schultz, H. Kunz, Chem. Rev., 2000, 100, 4495.
[89] S.A. Svarovsky, J.J. Barchi, Jr., Carbohydr. Res., 2003, 338, 1925.
[90] M. Tingoli, M. Tiecco, D. Chianelli, R. Balducci, A. Temperini, J. Org. Chem., 1991, 56, 6809.
[91] S. Czernecki, E. Ayadi, D. Randriamandimby, J. Org. Chem., 1994, 59, 8256.
[92] F. Santoyo-González, F.G. Calvo-Flores, P. Garcia-Mendoza, F. Hernández-Mateo, J. Isac-Garcia, R. Robles-Diaz, J. Org. Chem., 1993, 58, 6122.
[93] S. Mehta, B.M. Pinto, J. Org. Chem., 1993, 58, 3269.
[94] S. Yamago, T. Yamada, O. Hara, H. Ito, Y. Mino, J. Yoshida, Org. Lett., 2001, 3, 3867.
[95] W.-T. Jiaang, M.-Y. Chang, P.-H. Tseng, S.-T. Chen, Tetrahedron. Lett., 2000, 41, 3127.
[96] Y.V. Mironov, A.A. Sherman, N.E. Nifantiev, Tetrahedron Lett., 2004, 45, 9107.
[97] D.A. Griffith, S.J. Danishefsky, J. Am. Chem. Soc., 1990, 112, 5811.
[98] U. Iserloh, V. Dudkin, Z.-G.Wang, S.J. Danishefsy, Tetrahedron Lett., 2002, 43, 7027.
[99] D.A. Griffith, S.A. Danishefsky, J. Am. Chem. Soc., 1991, 113, 5863.
[100] D.A. Griffith, S.A. Danishefsky, J. Am. Chem. Soc., 1996, 118, 9526.
[101] Z.-G. Wang, X. Zhang, M. Visser, D. Live, A. Zatorski, U. Iserloh, K.O. Lloyd, S.J. Danishefsky, Angew. Chem. Int. Ed., 2001, 40, 1728.
[102] V.Y. Dudkin, J.S. Miller, S.J. Danishefsy, Tetrahedron Lett., 2003, 44, 1791.
[103] J. Du Bois, C.S. Tomooka, J, Hong, E.M. Carreira, J. Am. Chem. Soc., 1997, 119, 3179.
[104] F.P. Boulineau, A.Wei, Carbohydr. Res., 2001, 334, 271.
[105] V.D. Bussolo, J. Liu, L. Huffman, D.Y. Gin, Angew. Chem. Int. Ed., 2000, 39, 204.
[106] J. Liu, D.Y. Gin, J. Am. Chem. Soc., 2002, 124, 9789.
[107] J. Liu, V. Di Bussolo, D.Y. Gin, Tetrahedron Lett., 2003, 44, 4015.
[108] R.L. Halcomb, S.J. Danishefsky, J. Am. Chem. Soc., 1989, 111, 6661.
[109] K. K.-C. Liu, S.J. Danishefsky, J. Org. Chem., 1994, 59, 1895.
[110] T.K. Park, I.J. Kim, S.J. Danishefsky, Tertahedron. Lett., 1995, 36, 9089.
[111] C.M. Timmers, M. Dekker, R.C. Buijsman, G.A. van der Marel, B. Ethell, G. Anderson, B. Burchell, G.J. Mulder, J.H. van Boom, Bioorg. Med. Chem. Lett., 1997, 7, 1501.
[112] D.A. Evans, B.W. Trotter, B. Côté, Tetrahedron Lett., 1998, 39, 1709.
[113] J.D. Rainier, J.M. Cox, Org. Lett., 2000, 2, 2707.
[114] Ch. Ernst, W. Klaffke, Tetrahedron Lett., 2001, 42, 2973.
[115] Ch. Ernst, M. Piacenza, S. Grimme, W. Klaffke, Carbohydr. Res., 2003, 338, 231.
[116] H.M.I. Osborn, T.H. Khan, Tetrahedron, 1999, 55, 1807.
[117] G.J.S. Lohman, P.H. Seeberger, J. Org. Chem., 2003, 68, 7541.
[118] V. Di Bussolo, Y.-J. Kim, D.Y. Gin, J. Am. Chem. Soc., 1998, 120, 13515.
[119] J.-Y. Kim, V. Di Bussolo, D.Y. Gin, Org. Lett., 2001, 3, 303.
[120] Y.-J. Kim, D.Y. Gin, Org. Lett., 2001, 3, 1801.
[121] W. Priebe, A. Zamojski, Tetrahedron, 1980, 36, 287.
[122] R. Blattner, R.J. Ferrier, R.H. Furneaux, Tetrahedron Asymm., 2000, 11, 379.
[123] B. Doboszewski, N. Blaton, P. Herdewijn, J. Org. Chem., 1995, 60, 7909.
[124] R.J. Ferrier, N. Prasad, J. Chem. Soc. (C), 1969, 570.
[125] E. Wieczorek, J. Thiem, Carbohydr. Res., 1998, 307, 263.
[126] Z.J. Liu, M. Zhou, J.M. Min, L.H. Zhang, Tetrahedron Asymm., 1999, 2119.
[127] G. Grynkiewicz, W. Priebe, A. Zamojski, Carbohydr. Res., 1979, 68, 33.
[128] S. Danishefsky, J.F. Kerwin, Jr., J. Org. Chem., 1982, 47, 3803.
[129] J.S. Yadav, B.V.S. Reddy, J.V. Raman, N. Niranjan, S. Kiran Kumar, A.C. Kunwar, Tetrahedron Lett., 2002, 43, 2095.
[130] M. Takhi, A.A.-H. Abdel Rahman, R.R. Schmidt, Tetrahedron Lett., 2001, 42, 4053.
[131] S. Hotha, A. Tripathi, Tetrahedron Lett., 2005, 4555.
[132] P. Tiwari, G. Agnihotri, A.K. Misra, Carbohydr. Res., 2005, 340, 749.
[133] S. Xue, L. He, K.-Z. Han, X.Q. Zheng, Q.-X. Guo, Carbohydr. Res., 2005, 340, 303.
[134] B.S. Babu, K.K. Balasubramanian, Tetrahedron Lett., 1999, 40, 5777.
[135] E. Wieczorek, J. Thiem, Polish J. Chem., 1999, 73, 1111.
[136] A.L.J. Byerley, A.M. Kenwright, P.G. Steel, Tetrahedron Lett., 1996, 37, 9093.
[137] B. Doboszewski, N. Blaton, P. Herdewijn, Tetrahedron Lett., 1995, 36, 1321.
[138] S. Chandrasekhar, Ch.R. Reddy, G. Chandrashekar, Tetrahedron Lett., 2004, 45, 6481.
[139] H. Kawabata, S. Kubo, M. Hayashi, Carbohydr. Res., 2001, 333, 153.
[140] J.S. Yadav, B.V. S. Reddy, P.K. Chand, Tetrahedron Lett., 2001, 42, 4057.
[141] A. Takano, H. Fukuhara, T. Ohno, M. Kutsuma, T. Fujimoto, H. Shirai, R. Iriye, A. Kakehi, I. Yamamoto, J. Carbohydr. Chem., 2003, 22, 443.
[142] B. Liberek, Z. Smiatacz, Polish J. Chem., 2000, 74, 989.
[143] A. Banaszek, A. Zamojski, Polish J. Chem., 1979, 53, 2029.
[144] H.H. Baer, L. Siemsen, Carbohydr. Res., 1986, 146, 63.
[145] R.J. Ferrier, N. Prasad, J. Chem. Soc. (C), 1969, 575.
[146] P.H. Gross, Carbohydr. Polym., 1998, 37, 215.
[147] F. Gonzalez, S. Lesage, A. Perlin, Carbohydr. Res., 1975, 42, 267.
[148] P. Hansen, J. Lau, E.B. Pedersen, C.M. Nielsen, Liebigs Ann. Chem., 1990, 1079.
[149] E.B. Pedersen, J. Wengel, Synthesis, 1991, 451.
[150] L. Daley, P. Roger, C. Monneret, J. Carbohydr. Chem., 1997, 16, 25.
[151] A. Dąbrowska, P. Dokurno, A. Konitz, Z. Smiatacz, Carbohydr. Res., 2000, 323, 230.
[152] B. Liberek, A. Dąbrowska, R. Frankowski, Z. Smiatacz, J. Carbohydr. Chem., 2004, 23, 417.
[153] B. Liberek, A. Dąbrowska, R. Frankowski, M. Matuszewska, Z. Smiatacz, Carbohydr. Res., 2002, 337, 1803.
[154] J.-C. Florent, C. Monneret, J. Chem. Soc., Chem. Commun., 1987, 1171.
[155] B. Abbaci, J.-C. Florent, C. Monneret, J. Chem. Soc., Chem. Commun., 1989, 1896.
[156] B. Abbaci, J.-C. Florent, C. Monneret, Carbohydr. Res., 1992, 228, 171.
[157] J. Wengel, J. Lau, E.B. Pedersen, C. M. Nielsen, J. Org. Chem., 1991, 56, 3591.
[158] R. Sagar, R. Pathak, A.K. Shaw, Carbohydr. Res., 2004, 339, 2031.
[159] M. Yu, B.L. Pagenkopf, Tetrahedron, 2005, 61, 321.
[160] R. Murali, C.V. Ramana, M. Nagarajan, J. Chem. Soc., Chem. Commun., 1995, 217.
[161] J. Furukawa, N. Kawabata, J. Nishimura, Tetrahedron, 1968, 24, 53.
[162] J.O. Hoberg, J.J. Bozell, Tetrahedron Lett., 1995, 36, 6831.
[163] J.O. Hoberg, J. Org. Chem., 1997, 62, 6615.
[164] R.W. Scott, C.H. Heathcock, Carbohydr. Res., 1996, 291, 205.
[165] C.V. Ramana, R. Murali, M. Nagarajan, J. Org. Chem., 1997, 62, 7694.
[166] K.J. Henry Jr., B. Fraser-Reid, Tetrahedron Lett., 1995, 36, 8901.
[167] J.O. Hoberg, D.J. Claffey, Tetrahedron Lett., 1996, 37, 2533.
[168] C.M. Timmers, M.A. Leeuwenburgh, J.C. Verheijen, G.A. van der Marel, J.H. van Boom, Tetrahedron Asymm., 1996, 7, 49.
[169] Y. Leblanc, B.J. Fitzsimmons, J.P. Springer, J. Rokach, J. Am. Chem. Soc., 1989, 111, 2995.
[170] Y. Leblanc, B.J. Fitzsimmons, Tetrahedron Lett., 1989, 30, 2889.
[171] S.J. Danishefsky, S.L. DeNinno, S.-H. Chen, L. Boisvert, M. Barbachyn, J. Am. Chem. Soc., 1989, 111, 5810.
[172] G. Capozzi, Ch. Falciani, S. Menichetti, C. Nativi, R.W. Franck, Tetrahedron Lett., 1995, 36, 6755.
[173] G. Capozzi, A. Dios, R.W. Franck, A. Geer, C. Marzabadi, S. Menichetti, Ch. Nativi, M. Tamarez, Angew. Chem. Int. Ed. Engl., 1996, 35, 777.
[174] R.W. Franck, C.H. Marzabadi, J. Org. Chem., 1998, 63, 2197.
[175] G. Capozzi, F. Mannocci, S. Menichetti, C. Nativi, S. Paoletti, Chem. Commun., 1997, 2291.
[176] G. Capozzi, S. Giannini, S. Manichetti, C. Nativi, A. Giolitti, R. Patacchini, E. Perrotta, M. Altamura, C.A. Maggi, Bioorg. Med. Chem. Lett., 2002, 12, 2263.
[177] C.H. Marzabadi, R.W. Franck, R.F. Schinazi, Bioorg. Med. Chem. Lett., 2002, 10, 273.
[178] M.M. Tamarez, R.W. Franck, A. Geer, Tetrahedron, 2003, 59, 4249.
[179] F. Cardona, S. Valenza, A. Goti, A. Brandi, Tetrahedron Lett., 1997, 38, 8097.
[180] J. Oh, Ch. R. Lee, K.H. Chun, Tetrahedron Lett., 2001, 42, 4879.
[181] J.S. Yadav, B.V.S. Reddy, L. Chandraiah, B. Jagannadh, S.K. Kumar, A.C. Kunwar, Tetrahedron Lett., 2002, 43, 4527.

Typ dokumentu

Bibliografia

Identyfikator YADDA

bwmeta1.element.baztech-article-BUS2-0010-0020