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2005 | 3 | 1 | 118-136
Tytuł artykułu

Studies on stereoselective approaches to β-carboline derivatives

Treść / Zawartość
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
Transformation of β-carboline derivatives into optically active entities were studied and the de and ee values of the resulted compounds were detected.
Wydawca

Czasopismo
Rocznik
Tom
3
Numer
1
Strony
118-136
Opis fizyczny
Daty
wydano
2005-03-01
online
2005-03-01
Twórcy
  • Department of Organic Chemistry, University of Technology and Economics, Gellért tér 4, H-1111, Budapest, Hungary
  • Research Group for Alkaloid Chemistry, Hungarian Academy of Sciences, Gellért tér 4, Hungary
  • Department of Organic Chemistry, University of Technology and Economics, Gellért tér 4, H-1111, Budapest, Hungary
  • Department of Organic Chemistry, University of Technology and Economics, Gellért tér 4, H-1111, Budapest, Hungary
autor
  • Department of Organic Chemistry, University of Technology and Economics, Gellért tér 4, H-1111, Budapest, Hungary
  • Central Research Center, Hungarian Academy of Sciences, P.O. Box 17, H-1525, Budapest, Hungary
Bibliografia
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  • [3] N. Qais, N. Nakao, K. Hashigaki, Y. Takeuchi and M. Yamato: “Symmetric synthesis of 1-alkyltetrahydro-β-carbolines and a 9-thio analogue”, Chem. Pharm. Bull., Vol. 39, (1991), pp. 3338–3340;
  • [4] A.W.M. Lee, W.H. Chan, Y. Tao and Y.K. Lee: “Chiral acetylenic sulfoxide in enantioselective synthesis of tetrahydroisoquinoline and tetrahidro-β-carboline alkaloids. Total synthesis of (R)-(+)-carnegine and (R)-(+)-tetrahydroharman”. J. Chem. Soc., Perkin Trans 1, (1994), pp. 477–481; http://dx.doi.org/10.1039/p19940000477[Crossref]
  • [5] S. Adam, X. Pannecoucke, J.-C. Combret and J.-C. Quirion: “Diastereoselective alkylation of 2,3,4,6-di-O-isopropylidene-2-keto-L-gulonic amides. Application to the asymmetric synthesis of 1-substituted-1,2,3,4-tetrahydroisoquinolines and 1-substituted-1,2,3,4-tetrahydro-β-carbolines”, J. Org. Chem., Vol. 66, (2001), pp. 8744–8750. http://dx.doi.org/10.1021/jo0155658[Crossref]
  • [6] For asymmetric Pictet-Spengler reaction, see: T. Shoe, T. Kawate, N. Fukui, T. Hino and M. Nakagawa: “Asymmetric Pictet-Spengler reaction using α-methylbenzylamine as a chiral auxiliary group”, Heterocycles, Vol. 42, (1996), pp. 347–358
  • [7] H. Yamada, T. Kawate, M. Matsumizu, A. Nishida, K. Yamaguchi and M. Nakagawa: “Chiral Lewis acid-mediated enantioselective Pictet-Spengler reaction of N b -hydroxytriptamine with aldehydes”, J. Org. Chem., Vol. 63, (1998), pp. 6348–6394 http://dx.doi.org/10.1021/jo980810h[Crossref]
  • [8] T. Kawate, M. Yamanaka and M. Nakagawa: “Chiral auxiliary approach to the asymmetric Pietet-Spengler reaction of triptamines”, Heterocycles, Vol. 50, (1999), pp. 1033–1039 http://dx.doi.org/10.3987/COM-98-S(H)106[Crossref]
  • [9] R. Tsuji, M. Nakagawa and A. Nishida: “An efficient synthetic approach to optically active β-carboline derivatives via Pictet-Spengler reaction promoted by trimethylchlorosilane”, Tetrahedron Asymmetry, Vol. 14, (2003), pp. 177–180. http://dx.doi.org/10.1016/S0957-4166(02)00793-0[Crossref]
  • [10] For asymmetric reduction, see: K. Yamada, M. Takeda and T. Iwakuma: “A novel asymmetric reduction of imines with chiral sodium triacyloxyborohydrides”, Tetrahedron Lett., Vol. 22, (1981), pp. 3869–3872 http://dx.doi.org/10.1016/S0040-4039(01)91331-0[Crossref]
  • [11] K. Yamada, M. Takeda and T. Iwakuma: “Asymmetric reduction of cyclic imines with chiral sodium acyloxyborohydrides”, J. Chem. Soc., Perkin Trans., 1, (1983), pp. 265–270 http://dx.doi.org/10.1039/p19830000265[Crossref]
  • [12] N. Uematsu, A. Fujii, S. Hashiduchi, T. Ikarya and R. Noyori: “Asymmetric transfer hydrogenation of imines”, J. Am. Chem. Soc., Vol. 118, (1996), pp. 4916–4917 http://dx.doi.org/10.1021/ja960364k[Crossref]
  • [13] A.R. Hajipour and M. Hantehzadeh: “Asymmetric reduction of prochiral cyclic imines to alkaloid derivatives by novel asymmetric reducing agent in THF or under solid-state conditions.”, J. Org. Chem., Vol. 64, (1999), pp. 8475–8478. http://dx.doi.org/10.1021/jo990267k[Crossref]
  • [14] G. Blaskó, K. Honty, L. Novák and Cs. Szántay: “A simple synthesis of octahydroindolo[2,3-a]quinolizin-2-one”, Acta Chim. Acad. Sci. Hung., Vol. 99, (1979), pp. 35–41.
  • [15] L. Hazai, M. Milen, P. Kolonits, A. Dobó and Cs. Szántay: “Preferred carbon vs. nitrogen sulfonylation on β-carbolines”, Synth. Commun., Vol. 31, (2001), pp. 919–927. http://dx.doi.org/10.1081/SCC-100103328[Crossref]
  • [16] C. Nájera, and M. Yus: “Desulfonylation reactions: recent developments”, Tetrahedron, Vol. 55, (1999), pp. 10547–10658 and references cited therein. http://dx.doi.org/10.1016/S0040-4020(99)00600-6[Crossref]
  • [17] S. Becker, Y. Fort and P. Caubere: “New desulfurizations by nickel-containing complex reducing agents”, J. Org. Chem., Vol. 55, (1990), pp. 6194–6198. http://dx.doi.org/10.1021/jo00312a029[Crossref]
  • [18] J. Fekete, M. Milen, L. Hazai, L. Poppe, Cs. Szántay, A. Kettrup and I. Gebefügi: “Comparative study on separation of diastereomers by HPLC”, Chromatographia, Vol. 57, (2003), pp. 147–153. http://dx.doi.org/10.1007/BF02491708[Crossref]
  • [19] Atta-ur-Rahman: “Reactions of harmaline (4,9-dihydro-7-methoxy-1-methyl-3H-pyrido[3,4-b]indole) and its derivatives. II”, J. Chem. Soc., Perkin Trans., 1, (1972), pp. 736–738
  • [20] J. Laronze, J.Y. Laronze, M. Garnier, C. Trentesaux and J. Lévy: “An improved synthesis of naucletine”, Bull. Soc. Chim. Fr., Vol. 129, (1992), pp. 303–307.
  • [21] H.J.R. Lucas and W. Baumgarten: “The reduction of tartaric acid”, J. Am. Chem. Soc., Vol. 63, (1941), pp. 1653–1657. http://dx.doi.org/10.1021/ja01851a043[Crossref]
  • [22] C.L. Butler and L.H. Cretcher: “Note on the preparation of dibenzoyl-d-tartaric acid”, J. Am. Chem. Soc., Vol. 55, (1933), pp. 2605–2606. http://dx.doi.org/10.1021/ja01333a507[Crossref]
  • [23] L. Duhamel, T. Herman and P. Angiband: “An easy access to (3R,4R)-O,O-diacyltartrimides”, Synth. Commun., Vol. 22, (1992), pp. 735–740.
  • [24] T. Itoh, K. Nagata, M. Miyazaki, K. Kameoka and A. Ohsawa: “Asymmetric addition of nucleophiles to C-1 position of isoquinolines using (S)-alanine derivatives as chiral auxiliaries”, Tetrahedron, Vol. 57, (2001), pp. 8827–8839. http://dx.doi.org/10.1016/S0040-4020(01)00881-X[Crossref]
  • [25] U. Schmidt, M. Kroner and U. Beutler: “Amino acides and peptides. 67. Easy preparation and use of benzyloxycarbonyl derivatives of amino acid chlorides and α-hydroxycarboxylic acid chlorides”, Synthesis, (1988), pp. 475–477.
  • [26] J. Cuesta, G. Arsequell, G. Valencia and A. Gonzales: “Photochemical desulfurization of thiols and disulfides”, Tetrahedron Asymmetry, Vol. 10, (1999), pp. 2643–2646 http://dx.doi.org/10.1016/S0957-4166(99)00265-7[Crossref]
  • [27] M. Calmes, J. Daunis, R. Jacquier and J. Verducci: “A general and accurate nmr determination of the enantiomeric purity of α-aminoacids and α-aminoacid derivatives”, Tetrahedron, Vol. 43, (1987), pp. 2285–2292. http://dx.doi.org/10.1016/S0040-4020(01)86812-5[Crossref]
  • [28] W.H. Pirkle, P.G. Murray, D.J. Rausch and S.T. McKenna: “Intermolecular 1H-1H two-dimensional nuclear Overhauser enhancements in the characterization of a rationally designed chiral recognition system”, J. Org. Chem., Vol. 61, (1996), pp. 4769–4774. http://dx.doi.org/10.1021/jo951255b[Crossref]
  • [29] H.H. Myung, H. Seung-Ryul and R. Jae-Jeong: “New chiral stationary phases with two centers for the liquid chromatographic resolution of racemic anti-inflammatory drugs related to α-arylpropionic acids”, Chem. Lett., (1994), pp. 1021–1024.
  • [30] G.R. Pettit, S.B. Singh, D.L. Herald, P. Lloyd. Williams, D. Kantoci, D.D. Burkett, J. Barkóczy, F. Hogan and T.R. Wardlaw: “The dolastatins. 17. Synthesis of dolaproine and related diastereomers”, J. Org. Chem., Vol. 59, (1994), pp. 6287–6295. http://dx.doi.org/10.1021/jo00100a034[Crossref]
  • [31] R. Tschesche, H. Jenssen and P. N. Rangachari: “Über Umsetzungsprodukte des L-Tryptophans bei der sauren Eiweißhydrolyse”, Chem. Ber., Vol. 91, (1958), pp. 1732–1744. [Crossref]
  • [32] K. Tomohiko, N. Masako, Y. Hitoshi, H. Mariko and H. Tohru: “Alkylation of 3,4-dihydro-β-carboline”, Chem. Pharm. Bull., Vol. 41, (1993), pp. 287–291.
  • [33] Z. Czarnocki, D.B. MacLean and W.A. Szarek: “Diastereoselective reduction of derivatives of 3,4-dihydro-1-methylidene-2-tartaroylisoquinoline”, Heterocycles, Vol. 34, (1992), pp. 943–953. http://dx.doi.org/10.3987/COM-91-5959[Crossref]
Typ dokumentu
Bibliografia
Identyfikatory
Identyfikator YADDA
bwmeta1.element.-psjd-doi-10_2478_BF02476243
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