Synthesis of C-1 indol-3-yl substituted tetrahydroisoquinoline derivatives via a Pictet-Spengler approach

Tetrahedron Letters

Volumn 53, Issue 37, 2012, Pages 4966-4970

  Larsson, Rikard ^a   Blanco, Narda ^a   Johansson, Martin ^a   Sterner, Olov ^a  

^a LUND UNIVERSITY   (Sweden)

Author keywords

1H Indole 3 carbaldehydes; C 1 Indolyl tetrahydroisoquinolines; Diketopiperazine fused tetrahydroisoquinolines; l DOPA; Pictet Spengler condensation

Indexed keywords

TETRAHYDROISOQUINOLINE DERIVATIVE;

ACYLATION; DRUG SYNTHESIS; HYDROPHILICITY; NUCLEAR OVERHAUSER EFFECT; PICTET SPENGLER REACTION; RACEMIZATION; REVIEW; ROOM TEMPERATURE; STEREOCHEMISTRY;

EID: 84865034915     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.07.017     Document Type: Article

References (15)

1. J.D. Scott, and R.M. Williams Chem. Rev. 102 2002 1669 1730
2. S. Aubry, S. Pellet-Rostaing, M. Lemaire, and R. Faure J. Heterocycl. Chem. 43 2006 139 148
3. A. Pictet, and T. Spengler Ber. Dtsch. Chem. Ges. 44 1911 2030 2036
4. S.D. Edmondson, and S.J. Danishefsky Angew. Chem., Int. Ed. 37 1998 1138 1140
5. P.D. Bailey, P.D. Clingan, T.J. Mills, R.A. Price, and R.G. Pritchard Chem. Commun. 2003 2800 2801
6. S.L. Bogza, K.I. Kobrakov, A.A. Malienko, I.F. Perepichka, S.Y. Sujkov, M.R. Bryce, S.B. Lyubchik, A.S. Batsanovc, and N.M. Bogdana Org. Biomol. Chem. 3 2005 932 940
7. M.M.D. Numa, L.V. Lee, C.-C. Hsu, K.E. Bower, and C.-H. Wong ChemBioChem 6 2005 1002 1006
8. P.D. Bailey, M.H. Moore, K.M. Morgan, D.I. Smith, and J.M. Vernon Tetrahedron Lett. 35 1994 3587 3588
9. K. Singh, P.K. Deb, and P. Venugopalan Tetrahedron 57 2001 7939 7949
10. J. Stöckigt, A.P. Antonchick, F. Wu, and H. Waldmann Angew. Chem., Int. Ed. 50 2011 8538 8564
11. M. Lorenz, M.L. Van Linn, and J.M. Cook Curr. Org. Synth. 7 2010 189 223
12. Y. Wang, Z.Z. Liu, S.Z. Chen, and X.T. Liang Chin. Chem. Lett. 5 2004 505 507
13. P.D. Bailey, M.A. Beard, and T.R. Phillips Tetrahedron Lett. 50 2009 3645 3647
14. J. Ma, W. Yin, H. Zhou, X. Liao, and J.M. Cook J. Org. Chem. 74 2009 264 273
15. J. Van der Eycken, J.-P. Bosmans, D. Van Haver, M. Vandewalle, A. Hulkenberg, W. Veerman, and R. Nieuwenhuizen Tetrahedron Lett. 30 1989 3873 3876