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A new approach to 3-substituted tetrahydro-β-carboline derivative via diethyl acetamidomalonate

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Abstract

Strategically a new approach for the synthesis tetrahydro-β-carboline unit with the aid of diethyl acetamidomalonate as a glycine equivalent has been described.

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References

  • Bailey PD, Hollinshead SP (1988) Application of a modified Pictet–Spengler reaction to the synthesis of optically active tetrahydro-β-carbolines, key intermediates in the preparation of many indole alkaloids. J Chem Soc Perkin Trans 1:739–745

    Article  Google Scholar 

  • Chopra RN, Gupta JC, Mukherjee B (1933) The pharmacological action of an alkaloid obtained from Rauvolfia serpentina. Indian J Med Res 21:261–271

    CAS  Google Scholar 

  • Cook JM, Cox ED (1995) The Pictet–Spengler condensation: a new direction for an old reaction. Chem Rev 95:1797–1842 (and references cited therein)

    Article  Google Scholar 

  • Cook JM, Yin W, Kabir MS, Wang Z, Rallapalli SK, Ma J (2010) Enantiospecific total synthesis of the important biogenetic intermediates along the ajmaline pathway, (+)-polyneuridine and (+)-polyneuridine aldehyde, as well as 16-epivellosimine and macusine A. J Org Chem 75:3339–3349

    Article  PubMed  Google Scholar 

  • Fujii N, Ohno H, Oishi S, Ohta Y (2009) Facile synthesis of 1,2,3,4-tetrahydro-β-carbolines by one-pot domino three-component indole formation and nucleophilic cyclization. Org Lett 11:1979–1982

    Article  PubMed  Google Scholar 

  • Ho TL, Lin QX (2008) Stereoselective synthesis of (±)-tacamonine. Tetrahedron 64:10401–10405

    Article  CAS  Google Scholar 

  • Jenkins PR, Wilson J, Emmerson D, Garcia MD, Smith MR, Gray SJ, Britton RG, Mahale S, Chaudhuri B (2008) Design, synthesis and biological evaluation of new tryptamine and tetrahydro-β-carboline-based selective inhibitors of CDK4. Bioorg Med Chem 16:7728–7739

    Article  PubMed  CAS  Google Scholar 

  • Kotha S (2003) The building block approach to unusual α-amino acid derivatives and peptides. Acc Chem Res 36:342–351

    Article  PubMed  CAS  Google Scholar 

  • Kotha S, Halder S (2010) Ethyl isocyanoacetate as useful glycine equivalent. Synlett, 337–354

  • Kotha S, Singh K (2004) N-Alkylation of diethyl acetamidomalonate: synthesis of constrained amino acid derivatives by ring-closing metathesis reaction. Tetrahedron Lett 45:9607–9610

    Article  CAS  Google Scholar 

  • Kotha S, Misra S, Krishna NG, Devunuri N, Hopf H, Keecherikunne A (2010) Diversity oriented approach to 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Tic) derivatives using diethyl acetamidomalonate as a glycine equivalent. Further explansion by Suzuki–Miyaura cross-coupling reaction. Heterocycles 49:847–852

    Article  Google Scholar 

  • Liu Z, Xu F (1989) Total synthesis of N a-methyl-Δ18-isokoumidine, a possible precursor of the koumine type indole alkaloids. Tetrahedron Lett 30:3457–3460

    Article  CAS  Google Scholar 

  • Ma J, Yin W, Zhou H, Cook JM (2007) Total synthesis of the opioid agonistic indole alkaloid mitragynine and the first total syntheses of 9-methoxygeissoschizol and 9-methoxy-N b-methylgeissoschizol. Org Lett 9:3491–3494

    Article  PubMed  CAS  Google Scholar 

  • Magnus P, Gazzard L, Hobson L, Payne AH, Lynch V (1999) Studies on the synthesis of the indole alkaloids pauciflorine A and B. Tetrahedron Lett 40:5135–5138

    Article  CAS  Google Scholar 

  • Mergott DJ, Zuend SJ, Jacobsen EN (2008) Catalytic asymmetric total synthesis of (+)-yohimbine. Org Lett 10:745–748

    Article  PubMed  CAS  Google Scholar 

  • Moody CJ, Roffey JRA (2000) Synthesis of N-protected nortopsentins B and D. ARKIVOC 3:393–401

    Google Scholar 

  • Moody CJ, Jackson PM, Harrison CA, Williams MJ (1995) Cyclopenta [b] indoles. Part 2. Model studies towards the tremorgenic mycotoxins. J Chem Soc Perkin Trans 1:1131–1136

    Google Scholar 

  • Petter A, Engelmann K (1974) Antiarrhythmic action of ajmaline on the heart. Arzneim Forsch 24:876–880

    CAS  Google Scholar 

  • Pfeffer FM, Stewart SG, Priebbenow DL, Henderson LC (2010) Domino Heck–Aza-Michael reactions: efficient access to 1-substituted tetrahydro-β-carbolines. J Org Chem 75:1787–1790

    Article  PubMed  Google Scholar 

  • Shen Ya-C, Chen CY, Hsieh PW, Duh CY, Lin YM, Ko CL (2005) The preparation and evaluation of 1-substituted 1,2,3,4-tetrahydro- and 3,4-dihydro-β-carboline derivatives as potential antitumor agents. Chem Pharm Bull 53:32–36

    Article  PubMed  CAS  Google Scholar 

  • Shipman M, Hayes JF, Tarver GJ, Shiers JJ, Mumford PM (2008) Synthesis of 1,1-disubstituted tetrahydro-b-carbolines from 2-methyleneaziridines. Tetrahedron Lett 24:3489–3491

    Google Scholar 

  • Soderberg BCG, Dantale SW (2003) A novel palladium-catalyzed synthesis of β-carbolines: application in total synthesis of naturally occurring alkaloids. Tetrahedron 59:5507–5514

    Article  Google Scholar 

  • Srinivasan PC, Saroja B (1984) A simple route to indole-2,3-quinodimethane-A facile synthesis of carbazoles. Tetrahedron Lett 25:5429–5430

    Article  Google Scholar 

  • Szawkało J, Czarnocki SJ, Zawadzka A, Wojtasiewicz K, Leniewski A, Maurin JK, Czarnocki Z, Drabowicz J (2007) Enantioselective synthesis of some tetrahydroisoquinoline and tetrahydro-β-carboline alkaloids. Tetrahedron Asymmetry 18:406–413

    Article  Google Scholar 

  • Verma PP, Sherigara BS, Mahadevan KM, Hulikal VK (2009) Efficient and straightforward synthesis of tetrahydrocarbazoles and 2,3-dimethylindoles catalyzed by CAN. Synth Commun 39:158–165

    Article  Google Scholar 

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Acknowledgments

We are grateful to DST and CSIR for the financial support and SAIF Mumbai for providing the spectral data. S. M. thank CSIR (New Delhi) for the award of research fellowship. S. K. thank DST for the award of J. C. Bose fellowship.

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Correspondence to Sambasivarao Kotha.

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Kotha, S., Misra, S. & Mobin, S.M. A new approach to 3-substituted tetrahydro-β-carboline derivative via diethyl acetamidomalonate. Amino Acids 41, 933–936 (2011). https://doi.org/10.1007/s00726-010-0792-z

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  • DOI: https://doi.org/10.1007/s00726-010-0792-z

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