Synteza polihydroksyindolizydyn z L,B-nienasyconych [delta]-laktonów

Rabiczko, J.; Socha, D.; Jurczak, M.; Chmielewski, M.

Artykuł - szczegóły

Tytuł artykułu

Synteza polihydroksyindolizydyn z L,B-nienasyconych [delta]-laktonów

Autorzy

Rabiczko J. , Socha D. , Jurczak M. , Chmielewski M.

Wybrane pełne teksty z tego czasopisma

Identyfikatory

Warianty tytułu

Synthesis of polyhydroxyindolizidines from L,B-unsaturated [delta]-lactones

Języki publikacji

Abstrakty

The isolation, synthesis and biological properties of polyhydroxylated alkaloids (iminosugars) constitute a well-visible trend in organic chemistry nowadays. Due to their structural resemblance to sugars, iminosugars are recognized by glycosidases, the enzymes that catalyse the hydrolysis of glycosidic bonds in carbohydrates and glycoconjugates. Since glycosidases play a very important role in many biological systems, the iminosugars which inhibit them display interesting biological activities. Indolizidines represented by castanospermine, swainsonine and lentiginosine are particularly interesting as they exhibit a variety of important biomedical properties. The present paper is not a survey of the literature, but only deals with syntheses towards lentiginosine, with the aim of illustrating representative approaches in the syntheses of polyhydroxyindolizidines. The high stereoselectivity of both the conjugate addition of hydrazine and the (1,3)-dipolar cycloaddition of nitrones to the a,b-unsaturated sugar d-lactones, prompted us to use the adducts of both reactions as substrates for the syntheses of polihydroxyindolizidines. The conjugate addition offers a stereocontrolled entry to derivaties of both D- and L-2-pyrrolidineacetic acids which can be easily transformed into desired indolizidines. As an example, the syntheses of lentiginosine are demonstrated. The (1,3)-dipolar cycloaddition of Brandi's nitrone to the title lactones proceeded with high stereoselectivity in the case of D- and L-glycero lactones, whereas there was a high kinetic resolution in the case of racemic D,L-glycero lactone. It was shown that adducts can be easily transformed into lentiginosine, 7-hydroxylentiginosine and 7,8-dihydroxylentiginosine.

Słowa kluczowe

reakcja addycji reakcja cykloaddycji synteza lentiginozyny chemia węglowodanów

chemical reaction addition reaction

Wydawca

Polskie Towarzystwo Chemiczne

Czasopismo

Wiadomości Chemiczne

Rocznik

2002

Tom

[Z] 56, 7-8

Strony

561--583

Opis fizyczny

schem., bibliogr., 62 poz.

Twórcy

autor

Rabiczko J.

autor

Socha D.

autor

Jurczak M.

autor

Chmielewski M.

Instytut Chemii Organicznej Polskiej Akademii Nauk, ul. M.Kasprzaka 44/52, 01-224 Warszawa

Bibliografia

[1] G.WJ. Fleet, L.E. Fellows, B. Winchester, [w:] Bioactive Compounds from Plants, Eds. P.J Chadwick, J. March, J. Wiley&Sons, Chichester 1990, s. 112.
[2] A.E. Stütz, Iminosugars as Glycosidase Inhibitors. J. Wiley-VCh, Weinheim 1999.
[3] A. El Nemur, Tetrahedron, 2000. 56, 8579.
[4] J. Mieczkowski. J. Jurczak. M. Chmielewski, A. Zamojski, Carbohydr. Res., 1977, 56, 180.
[5] F.W. Lichtenthaler, S. Röninger, R Jarglis, Liebigs Ann. Chem., 1989, 1153.
[6] S. Maciejewski, I. Panfil, C. Bełżecki, M. Chmielewski, Tetrahedron, 1992, 48, 10363.
[7] D. Socha, M. Jurczak, M. Chmielewski, Tetrahedron Lett., 1995, 36, 135.
[8] D. Socha, M. Jurczak, M. Chmielewski, Tetrahedron, 1997, 53, 739.
[9] M. Jurczak, D. Socha, M. Chmielewski, Tetrahedron, 1996, 52, 1411.
[10] I. Panfil, J. Krajewski, P. Gluziński. L. Stefaniak M. Chmielewski, Tetrahedron, 1994,50, 7219.
[11] I. Panfil. S. Maciejewski. C. Bełżecki, M. Chmielewski, Tetrahedron Lett., 1989, 30, 1527: S. Maciejewski, I. Panfil, C. Bełżecki, M. Chmielewski, Tetrahedron, 1992, 48, 10363.
[12] M. Chmielewski, J. Jurczak, A. Zamojski, Tetrahedron, 1978, 34, 2977.
[13] K. Torsel, M.P. Tyagi, Acta Chem. Scand., 1997, B31, 237.
[14] B.D. Roth, W.H. Roark, Tetrahedron Lett., 1988, 29, 1255.
[15] S. Takano, Y. Shimazaki, M. Moriya, K. Ogasawora, Chem. Lett., 1990, 1177; B. Herradon, R. Bao, E. Fenuda. S. Valverde, J. Org. Chem.. 1996. 61, 1143.
[16] P. Deslongchamps. Stereoelectronic Effects in Organic Chemistry, Pergamon Press, Oxford 1983.
[17] I. Panfil, C. Bełżecki, Z. Urbańczyk-Lipkowska, M. Chmielewski, Tetrahedron, 1991, 47, 10087.
[18] M. Jurczak, J. Rabiczko, D. Socha, M. Chmielewski, F. Cardona, A. Goti, A. Brandi, Tetrahedron: Asymmetry, 2000,11, 2015.
[19] H. Gnichtel. L. Autenrieth-Ansorge, J. Dachman, P. Luger, A. Duda, J. Carbohydr. Chem., 1987,6,673.
[20] L.D. Hohenschutz, E.A. Bell, P.J. Jewess, D.P. Leworthy, R.J. Pryce, E. Arnold, J. Clardy, Phytochemistry, 1981, 20, 811.
[21] F.P Guengerich, S.J. DiMari, H.P. Broquist, J. Am. Chem. Soc., 1973, 95, 2055.
[22] I. Pastuszak, R.J. Molyneux, L.F. James, A.D. Elbein, Biochemistry, 1990, 29, 1886.
[23] R.J. Nash, L.E. Fellows, J.V. Dring, C.H. Stirton, D. Carter, M.P. Hegarty, E.A. Bell, Phytochemistry, 1988,27, 1403.
[24] B.L. Reinhart, K.M. Robinson. A.J. Payne, M.E. Wheatley, J.L. Fisher, P.S. Liu, W. Chang, Life Sei., 1987, 41, 2325.
[25] E. Tmscheit, W. Frommer, L. Junge, L. Müller, D.D. Schmidt, W. Wingender, Ang. Chem. Int. Ed., 1981, 20, 744.
[26] R. Pili, J. Chang, R.A. Partis, R.A. Mueller, F.J. Chrest, A. Passaniti, Cancer Res., 1995, 55, 2995.
[27] M.A. Spearman, B.C. Ballon, J.M. Gerrard, A.H. Greenberg. J.A.. Wright, Cancer Lett 1991, 60, 185.
[28] E.J. Nichols, R. Manger, S. Hakomori, A. Herscovics, L.R. Rohrschneider Mol. Cell. Biol., 1985, 5,3467.
[29] R.M. Ruprecht, S. Mullaney, J. Anderson, R. Bronson, J. Acquired Immune Defic. Syndr., 1989, 2, 149.
[30] B.D. Walker, M. Kowalski, W.C. Goh, K. Kozarsky, M. Krieger, C. Rosen, L.R. Rohrschneider, W.A. Haseltine, J. Sodroski, Proc. Natl. Acad. Sei. U.S.A., 1987, 84, 8120.
[31] A. L. Margolin, D.L. Delinck, M.R. Whalon, J. Am. Chem. Soc., 1990,112, 2849.
[32] R.J. Molyneux, J.N. Roitman, G. Dunnheim, T. Szumilo, A.D. Elbein, Arch. Biochem. Biophys., 1986, 251, 450.
[33] R.J. Molyneux, Y.T. Pan, J.E. Tropea, M. Benson, G.P. Kaushal, A.D. Elbein, Biochemistry. 1991, 30. 9981.
[34] a) V.M.D. Perez, M.I.G. Moreno, C.O. Mellet, J. Fuentes, J.C.D. Arribas, F.J. Canada. J.M.G. Fernandez, J. Org. Chem., 2000, 65, 136; b) U.K. Pandit, H.S. Overkleeft, B.C. Borer, H. Bieraugel, Eur. J. Org. Chem., 1999, 5, 959; c) E. Bartnicka, A. Zamojski, Tetrahedron, 1999, 55, 2061; d) S.E. Denmark, E.A. Martinborough, J. Am. Chem. Soc., 1999, 121, 3046; e) J. Izquierdo, M.T. Plaza, R. Robles, C. Rodriguez, A. Ramirez, A.J. Mota, Eur. J. Org. Chem., 1999, 6, 1269.
[35] K. Burgess, I. Henderson, Tetrahedron, 1992, 48, 4045.
[36] P. Herczeg, I. Koväcs, F. Sztaricskai, [w:] Recent Progress in the Chemical Synthesis o f Antibiotics and Related Microbial Products, Ed. G. Lukács; Springer-Verlag, Berlin, Heidelberg 1993, 2, 751.
[37] P.C. Tyler, B.G. Winchester, [w:] Iminosugars as Glycosidase Inhibitors, Nojirimycin and Beyond, Ed. A.E. Stütz, Wiley-VCH, Weinheim, 1999, s. 125.
[38] D.R.P. Tulsiani, T.M. Harris, O. Touster, J. Biol. Chem., 1982, 257, 7936.
[39] P.E. Goss, M.A. Baker, J.P. Carver, J.W. Dennis, Clin. Cancer. Res., 1995, 1, 935.
[40] P.E. Goss, C.L. Reid, D. Bailey, J.W. Dennis, Clin. Cancer. Res , 1997, 3, 1077.
[41] Y. Nashimura, [w:] Studies in Natural Pmducts Chemistry, Ed. Atta-ur-Rahman, Elsevier, Amsterdam 1992, 10, 495.
[42] A. Goti, F. Cardona, A. Brandi, S. Picasso, P. Vogel, Tetrahedron: Asymmetry, 1996, 7, 1659.
[43] A. Brandi, S. Cicchi, F.M. Cordero, R. Frignoli, A. Goti, S. Picasso, P. Vogel, J. Org. Chem., 1995, 60, 6806.
[44] H. Yoda, H. Kitayama, T. Katagiri, K. Takabe, Tetrahedron: Asymmetry, 1993, 4, 1455.
[45] H. YoJa. M. Kawauchi, K. Takabe, Synlett, 1998, 137.
[46] D.-C. Ha, C-S. Yun, Y. Lee, J. Org. Chem., 2000, 65, 621.
[47] F. Cordero, S. Cicchi, A. Goti, A. Brandi, Tetrahedron Lett., 1994, 35, 949.
[48] S. Cicchi, I. Höld, A. Brandi, J. Org. Chem., 1993, 58, 5274.
[49] A. Goti, F. Cardona, A. Brandi, Synlett, 1996, 761.
[50] F. Cardona, A. Goti, S. Picasso, P. Vogel, A. Brandi, J. Carbohydr. Chem., 2000, 19, 585.
[51] A.E. McCaig, K.P. Meldrum, R.H. Wightman, Tetrahedron, 1998, 54, 9429.
[52] R. Giovannini, E. Marcantoni, M. Petrini, J. Org. Chem., 1995, 60, 5706.
[53] M.K. Guijar, L. Ghosh, M. Syamala, V. Jayasree, Tetrahedron Lett., 1994, 35, 8871.
[54] S. Nukui, M. Sodeoka, H. Sasai, M. Shibasaki, J. Org. Chem., 1995, 60, 398.
[55] F.W. Lichtenthaler, F.D. Klingler, P. Jarglis, Carbohydr. Res., 1984, 132, C-1.
[56] M. Chmielewski, J. Jurczak, S. Maciejewski, Carbohydr. Res., 1987, 165, 111.
[57] J. Rabiczko, M. Chmielewski, J. Org. Chem., 1999, 64, 1347.
[58] J. Rabiczko, Z. Urbanczyk-Lipkowska, M. Chmielewski, Tetrahedron, 2002, 58, 1433.
[59] S. Valverde, S. Garcia-Ochoa, M. Martin-Lomas, J. Chem. Soc. Chem. Commun., 1987, 1714.
[60] D. Socha, J. Rabiczko, D. Konern, Z. Urbanczyk-Lipkowska, M. Chmielewski, Carbohydr. Lett., 1997, 2, 349.
[61] M. Jurczak, J. Rabiczko, J. Socha, M. Chmielewski, F. Cardona, A. Goti, A. Brandi, Tetrahedron: Asymmetry, 2000,11, 2015.
[62] D. Socha, M. Jurczak, M. Chmielewski, Carbohydr. Res., 2001, 336, 315.

Typ dokumentu

Bibliografia

Identyfikator YADDA

bwmeta1.element.baztech-article-BUS1-0010-0074