A concise first total synthesis of narceine imide

Organic and Biomolecular Chemistry

Volumn 5, Issue 9, 2007, Pages 1466-1471

  Lamblin, Marc ^a   Couture, Axel ^a   Deniau, Eric ^a   Grandclaudon, Pierre ^a  

^a UNIV LILLE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALINITY; KETONES; SALTS; SYNTHESIS (CHEMICAL);

ARYLMETHYLENE; ISOQUINOLINIUM SALT; METALATION; NARCEINE IMIDE; SEQUENTIAL CONSTRUCTION;

POLYIMIDES;

EID: 34247636272     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b701661a     Document Type: Article

References (55)

1. G. Blaskó D. J. Gula M. Shamma J. Nat. Prod. 1982 45 105
2. J. Hodková Z. Veselý Z. Koblicová J. Holubek J. Trojánek Lloydia 1972 35 61
3. S. Collin A. Patiny D. P. Vercauteren B. Norberg G. Evrard F. Durant J. Crystallogr. Spectrosc. Res. 1991 21 431
4. antidopaminergic D4 activity: T. R. Belliotti and D. J. Wustrow, US Patent, 2000, 6087364
5. T. R. Belliotti D. J. Wustrow Chem. Abs. 2000 133 89548
6. protein kinase inhibiting activity: R. L. Hudkins, D. Reddy, J. Singh, R. Stripathy and T. L. Underiner, PCT Int. Appl., 2000, WO 0047583
7. R. L. Hudkins D. Reddy J. Singh R. Stripathy T. L. Underiner Chem. Abs. 2000 133 177158
8. ανβ3 receptor antagonist: M. E. Duggan, G. D. Hartman and W. F. Hoffman, PCT Int. Appl., 1997, WO 9737655
9. M. E. Duggan G. D. Hartman W. F. Hoffman Chem. Abs. 1997 127 331749
10. H. Sugimoto Y. Tsuchiya H. Sugumi K. Higurashi N. Karibe Y. Iimura A. Sasaki S. Araki Y. Yamanishi K. Yamatsu J. Med. Chem. 1992 35 4542
11. J. Wrobel A. Dietrich S. A. Woolson J. Millen M. McCaleb M. C. Harrison T. C. Hohman J. Sredy D. Sullivan J. Med. Chem. 1992 35 4613
12. Hisamitsu Pharmaceutical Co., Inc., Japan Kokai Tokyo Koho, 1980, JP 55149257 (Chem. Abs., 1981, 94, 174879)
13. H. J. Schmahl L. Dencker C. Plum I. Chahoud H. Nau Arch. Toxicol. 1996 11 749
14. C. Shinji S. Maeda K. Imai M. Yoshida Y. Hashimoto H. Miyachi Bioorg. Med. Chem. 2006 14 7625
15. Y. Kato M. Takemoto K. Achiva Chem. Pharm. Bull. 1993 41 2003
16. P. Pigeon B. Decroix Tetrahedron Lett. 1996 37 7707
17. K. Achinami, N. Ashizawa and F. Kobayashi, Jpn Patent, 1991, JP 03133955
18. K. Achinami N. Ashizawa F. Kobayashi Chem. Abs. 1991 115 255977
19. Laboratori Baldacci S. p. A., Jpn Patent, 1984, JP 59046268 (Chem. Abs., 1984, 101, 54922)
20. H. Paulová J. Ková J. Plocek J. Slavík Collect. Czech. Chem. Commun. 1987 52 2338
21. S. Pavelka J. Ková Collect. Czech. Chem. Commun. 1975 40 753
22. J. Fuska A. Fuskova B. Proksa, B. Neoplasma 1985 32 407
23. Z. Veselý J. Holubek J. Trojánek Collect. Czech. Chem. Commun. 1987 52 233
24. B. Proksa J. Fuska Pharmazie 1985 40 521
25. B. Proksa B. Steiner S. Uhrínová M. Koó Collect. Czech. Chem. Commun. 1987 52 233
26. B. Proksa Monatsh. Chem. 1993 124 953
27. M. Freund H. Michaels Liebigs Ann. Chem. 1895 286 248
28. M. Lamblin A. Couture E. Deniau P. Grandclaudon Synthesis 2006 1333
29. A. Moreau A. Couture E. Deniau P. Grandclaudon J. Org. Chem. 2004 69 4527
30. V. Rys A. Couture E. Deniau S. Lebrun P. Grandclaudon Synlett 2004 2233
31. V. Rys A. Couture E. Deniau P. Grandclaudon Eur. J. Org. Chem. 2003 1231
32. V. Rys A. Couture E. Deniau P. Grandclaudon Tetrahedron 2003 59 6615
33. A. Couture E. Deniau P. Grandclaudon H. Rybalko-Rosen S. Léonce B. Pfeiffer P. Renard Bioorg. Med. Chem. Lett. 2002 12 3537
34. A. Moreau M. Lorion A. Couture E. Deniau P. Grandclaudon J. Org. Chem. 2006 71 3303
35. M. Lamblin A. Couture E. Deniau P. Grandclaudon Tetrahedron 2006 62 2917
36. A. Moreau A. Couture E. Deniau P. Grandclaudon Eur. J. Org. Chem. 2005 3437
37. A. Moreau A. Couture E. Deniau P. Grandclaudon S. Lebrun Org. Biomol. Chem. 2005 3 2305
38. A. Moreau A. Couture E. Deniau P. Grandclaudon S. Lebrun Tetrahedron 2004 60 6169
39. A. Couture E. Deniau D. Ionescu P. Grandclaudon Tetrahedron Lett. 1998 39 2319
40. Z. Guo A. G. Schultz J. Org. Chem. 2001 66 2154
41. J. P. Heer J. D. Harling M. Thompson Synth. Commun. 2002 32 2555
42. T. Shirasaka Y. Takuma T. Shimpuku N. Imaki J. Org. Chem. 1990 55 3767
43. W. E. Parham C. K. Bradsher Acc. Chem. Res. 1982 15 300
44. B. J. Wakefield, The Chemistry of Organolithium Compounds, 2nd ed., Pergamon, New York, 1990
45. M. Gray, M. Tinkl and V. Snieckus, in Comprehensive Organometallic Chemistry II, E. W. Abel, F. G. A. Stone, and, G. Wilkinson, eds., Pergamon, Exeter, 1995, vol. 11, pp. 66-92
46. A. Ardeo, M. I. Collado, I. Osante, J. Ruiz, N. Sotomayor and E. Lete, in Targets in Heterocyclic Systems, O. Atanassi, and, D. Spinelli, eds., Italian Society of Chemistry, Rome, 2001, vol. 5, pp. 393-418
47. J. Clayden, Organolithiums: Selectivity for Synthesis, Elsevier Science Ltd, Oxford, 2002
48. M. J. Mealy W. F. Bailey J. Organomet. Chem. 2002 646 59
49. N. Sotomayor E. Lete Curr. Org. Chem. 2003 7 275
50. C. Nájera J. M. Sansano M. Yus Tetrahedron 2003 59 9255
51. M. C. de la Fuente D. Dominguez Tetrahedron 2004 60 10019
52. T. H. Lowry and K. S. Richardson, Mechanism and Theory in Organic Chemistry, 3rd edition, Harper and Row Publishers, New York, 1987, pp. 591-595
53. C. Subramanyan Synth. Commun. 1995 25 761
54. E. Fujita Y. Nagao K. Kaneko Chem. Pharm. Bull. 1978 26 3743
55. A. K. Sinhababu R. T. Borchardt J. Org. Chem. 1983 48 2356