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Studies on stereoselective approaches to β-carboline derivatives

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Central European Journal of Chemistry

Abstract

Transformation of β-carboline derivatives into optically active entities were studied and the de and ee values of the resulted compounds were detected.

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References

  1. F.A. Hochstein and A.M. Paradies: “Alkaloids of Banisteria caapi and Prestonia amazonicum”, J. Am. Chem. Soc., Vol. 79, (1957), pp. 5735–5736.

    Article  CAS  Google Scholar 

  2. M.F. Loewe and A.I. Meyers: “An asymmetric synthesis of indole alkaloids”, Tetrahedron Lett., Vol. 26, (1985), pp. 3291–3294;

    Article  CAS  Google Scholar 

  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;

    CAS  Google Scholar 

  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;

    Article  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  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

    Google Scholar 

  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

    Article  CAS  Google Scholar 

  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

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  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

    Article  CAS  Google Scholar 

  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

    Article  Google Scholar 

  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

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  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.

    Google Scholar 

  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.

    Article  CAS  Google Scholar 

  16. C. Nájera, and M. Yus: “Desulfonylation reactions: recent developments”, Tetrahedron, Vol. 55, (1999), pp. 10547–10658 and references cited therein.

    Article  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  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

    Google Scholar 

  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.

    CAS  Google Scholar 

  21. H.J.R. Lucas and W. Baumgarten: “The reduction of tartaric acid”, J. Am. Chem. Soc., Vol. 63, (1941), pp. 1653–1657.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  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.

    CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  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

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  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.

    CAS  Google Scholar 

  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.

    Google Scholar 

  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.

    Article  CAS  Google Scholar 

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Dedicated to Professor Károly Lempert on his 80th birthday.

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Milen, M., Hazai, L., Kolonits, P. et al. Studies on stereoselective approaches to β-carboline derivatives. cent.eur.j.chem. 3, 118–136 (2005). https://doi.org/10.2478/BF02476243

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  • DOI: https://doi.org/10.2478/BF02476243

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