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D-Ribono-1,4-lactone. Part 2, Use in organic synthesis – selected reactions
Języki publikacji
Abstrakty
There are many examples of syntheses with d-ribono-1,4-lactone as a substrate. Among all, its biggest advantage is undoubtedly its accessibility. It can be synthesized on a large scale from naturally available raw materials. Its characteristic feature is the stable configuration of individual carbon atoms in multiple reaction conditions. Very important is the presence of a carbonyl moiety, allowing for a variety of additions which is crucial for carbon-carbon bond formation, the most difficult synthesis in organic chemistry. In this article we present selected examples of articles that were published after 1984. In this year, the second article describing the Use of d-Ribonolactone in Organic Synthesis [36] was published. After this time many articles describing the use of the entitled lactone as a substrate in organic synthesis were published. We thought it would be worthwhile to present in Polish a selection of them. C-Glycosides and nucleoside analogs are a particularly important type of synthesized products. Examples of their synthesis are presented in this work, namely, neplanocin A [5], B [31] and F [24], citreovirdin [14], 2-bromopyridin α- and β-d-ribofuranosides [10], 4-deazaformicin A [27] and varitriol [ 33].
Wydawca
Czasopismo
Rocznik
Tom
Strony
861--885
Opis fizyczny
Bibliogr. 37 poz., schem
Twórcy
autor
- Wydział Chemii Uniwersytetu Gdańskiego, ul. Wita Stwosza 63, 80-308 Gdańsk
autor
- Wydział Chemii Uniwersytetu Gdańskiego, ul. Wita Stwosza 63, 80-308 Gdańsk
autor
- Wydział Chemii Uniwersytetu Gdańskiego, ul. Wita Stwosza 63, 80-308 Gdańsk
autor
- Wydział Chemii Uniwersytetu Gdańskiego, ul. Wita Stwosza 63, 80-308 Gdańsk
Bibliografia
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- [5] S. Yaginuma, N. Muto, M. Tsujino, Y. Sudate, M. Hayashi, M. Otani, J. Antibiot., 1981, 34, 359.
- [6] M. Hayashi, S. Yaginuma, H. Yoshioka, K. Nakatsu, J. Antibiot., 1981, 34, 675.
- [7] V.E. Marquez, M.I. Lim, C.K.H. Tseng, A. Markovac, M.A. Priest, M.S. Khan, B. Kaskar, J. Org. Chem., 1988, 53 , 5709.
- [8] J.C. Collins, W.W. Hess, F.J. Frank, Tetrahedron Lett., 1968, 9, 3363.
- [9] H. Ogura, H. Takahashi, J. Org. Chem., 1974, 39, 1374.
- [10] M.M. Kabat, K.W. Pankiewicz, E. Sochacka, K.A. Watanabe, Chem. Pharm. Bull., 1988, 36, 634.
- [11] H. Ogura, H. Takahashi, T. Itoh, J. Org. Chem., 1972, 37, 72.
- [12] R. Vleggaar, Pure Appl. Chem., 1986, 58, 1239.
- [13] (a) Y. Hirata, T. Goto, N. Sakabe, Tetrahedron Lett., 1964, 1825. (b) N. Sakabe, T. Goto, Y. Hirata, Tetrahedron, 1977, 33, 3077. (c) B. Frank, H. Gehrken, , Angew. Chem., Int. Ed. Engl., 1980, 19, 461.
- [14] H. Suh, C. S. Wilkox, J. Am. Chem. Soc., 1988, 110, 470.
- [15] T.V. RajanBabu, W.A. Nugent, D.F. Taber, P.J. Fagan, J. Am. Chem. Soc., 1988, 110, 7128.
- [16] Z. Czarnocki, J. Chem. Res., Synop., 1992, 334.
- [17] A. Bishler, B. Napieralski, Eur. J. I. Chem., 1893, 26, 1903.
- [18] E. Haslam, Shikimic acid: Metabolism and Metabolites, John Wiley, Chichester 1993.
- [19] a) M. Yoshikawa, Y. Ikeda, H. Kayakiri, I. Kitagawa, Heterocycles, 1982, 17, 209; b) G.W.J. Fleet, T.K.M. Shing, S.M. Warr, J. Chem. Soc. Perkin Trans, 1, 1984, 905; c) S. Mirza, J. Harvey, Tetrahedron Lett., 1991, 32, 4111; d) S. Mirza, A. Vasella, Helv. Chim. Acta, 1984, 67, 1562; e) T. Suami, K. Tadamo, Y. Ueno, Y. Iimura, Chem, Lett., 1985, 367.
- [20] S. Jiang, B. Mekki, G. Singh, R.H. Wightman, Tetrahedron Lett., 1994, 35, 5505.
- [21] P. Forns, M. Rubiralta, A. Díez, Contributions to Science, 2001, 2, 63.
- [22] J.F. Reichwein, R.M.J. Liskamp, Tetrahedron Lett., 1998, 39, 1243.
- [23] D. Fancelli, M.C. Fagnola, D. Severino, A. Bedeschi, Tetrahedron Lett., 1997, 38, 2311.
- [24] M.J. Comin, J. Leitofuter, J.B. Rodriguez, Tetrahedron, 2002, 58, 3129.
- [25] S. Rodriguez, D. Edmont, Ch. Mathé, Ch. Périgaud, Tetrahedron, 2007, 63, 7165.
- [26] M.J. Comin, J.B. Rodriguez, Tetrahedron, 2000, 56, 4639.
- [27] V.N. Kourafalos, P. Marakos, N. Pouli, L.B. Townsend, J. Org. Chem., 2003, 68, 6466.
- [28] A. Tarrade, P. Dauban, R.H. Dodd, J. Org. Chem., 2003, 68, 9521.
- [29] (a) P. Dauban, C. De Saint-Fuscien, R.H. Dodd, Tetrahedron, 1999, 55, 7589; (b) P. Dauban, C. De Saint-Fuscien, F. Acher, L. Prézeau, I. Brabet, J.-P. Pin, R.H. Dodd, Bioorg. Med. Chem. Lett., 2000, 10, 129.
- [30] M.S. Valle, A. Tarrade-Matha, P. Dauban, R.H. Dodd, Tetrahedron, 2008, 64, 419.
- [31] N. Hamon, J.-P. Uttaro, Ch. Mathé, Ch. Périgaud, Bioorg. Chem., 2010, 38, 275.
- [32] J. Malmstrom, C. Christophersen, A.F. Barrero, J.E. Oltra, J. Justicia, A. Rosales, J. Nat. Prod., 2002, 65, 364.
- [33] O. Karlubíková, M. Palík, A. Lásiková, T. Gracza, Synthesis, 2010, 3449.
- [34] O. Caletková, A. Lásiková, M. Hajdúch, P. Džubák, T. Gracza, Arkivoc, 2012, 365.
- [35] S.-Y. Chen, M. M. Joullié, Tetrahedron Lett., 1983, 24, 5027.
- [36] S.-Y. Chen, M.M. Joullié, J. Org. Chem., 1984, 49, 2168.
- [37] G.P. Silveira, H.M. Cardozo, T.A. Rossa, M.M. Sá, Curr. Org. Synth., 2015, 12, 584.
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-479f3418-c3dd-4c0c-a98b-d6255e1c284a