Asymmetric total synthesis of (+)-indatraline via diastereoselective amination of chiral ethers using chlorosulfonyl isocyanate

Tetrahedron

Volumn 69, Issue 7, 2013, Pages 1877-1880

  Lee, Sang Hwi ^a   Park, Sook Jin ^a   Kim, In Su ^a   Jung, Young Hoon ^a  

^a Sungkyunkwan University   (South Korea)

Author keywords

Amination; Asymmetric; CBS reduction; Chlorosulfonyl isocyanate; Indatraline; Total synthesis

Indexed keywords

CHLOROSULFONYL ISOCYANATE; CINNAMIC ACID; ETHER DERIVATIVE; INDATRALINE; ISOCYANIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; ASYMMETRIC SYNTHESIS; DRUG STRUCTURE; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 84872759985     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.12.044     Document Type: Article

References (33)

1. K.P. Bøgesø, J. Arnt, K. Frederiksen, H.O. Hansen, J. Hyttel, and H. Pedersen J. Med. Chem. 38 1995 4380
2. K.P. Bøgesø, J. Arnt, J. Hyttel, and H. Pedersen J. Med. Chem. 36 1993 2761
3. J. Guillon, P. Dallemagne, J.-M. Léger, J. Sopkova, P.R. Bovy, C. Jarry, and S. Rault Bioorg. Med. Chem. 10 2002 1043
4. K. Hyttel, and J.-J. Larsen J. Neurochem. 44 1985 1615
5. A. Graul, and J. Castaner Drugs Future 23 1998 903
6. J. Sterling, A. Veinberg, D. Lerner, W. Goldenberg, R. Levy, M. Youdim, and J. Finberg J. Neural Transm.Suppl. 52 1998 301
7. K.P. Bøgesø, J. Arnt, V. Boeck, A.V. Christensen, J. Hyttel, and K.G. Jensen J. Med. Chem. 31 1988 2247
8. B.K. Koe J. Pharmacol. Exp. Ther. 199 1976 649
9. J.H. Mendelson, and N.K. Mello N. Engl. J. Med. 334 1996 965
10. S.S. Negus, M.R. Brandt, and N.K. Mello J. Pharmacol. Exp. Ther. 291 1999 60
11. S. Rosenzweig-Lipson, J. Bergman, R.D. Spealman, and B.K. Madras Psychopharmacology 107 1992 186
12. K.P. Bøgesø, A.V. Christensen, J. Hyttel, and T. Liljefors J. Med. Chem. 28 1985 1817
13. M.F. Froimowitz, K.-M. Wu, A. Moussa, R.M. Haidar, J. Jurayj, C. George, and E.L. Gardner J. Med. Chem. 43 2000 4981
14. J. Cossy, D. Belotti, and A. Maguer Synlett 2003 1515
15. J.G.A. Walton, D.C. Jones, P. Kiuru, A.J. Durie, N.J. Westwood, and A.H. Fairlamb ChemMedChem 6 2011 321 For a reference on the formal synthesis of racemic indatraline, see
16. J.C. Pastre, and C.R.D. Correia Adv. Synth. Catal. 351 2009 1217
17. H.M.L. Davies, and T.M. Gregg Tetrahedron Lett. 43 2002 4951
18. S. Roesner, J.C. Casatejada, T.G. Elford., R.P. Sonawane, and V.K. Aggarwal Org. Lett. 13 2011 5740 For references on the asymmetric formal synthesis of (+)-indatraline, see
19. H.M.L. Davies, and A.M. Walji Org. Lett. 5 2003 479
20. K. Yoo, H. Kim, and J. Yun Chem. - Eur. J. 15 2009 11134
21. J.G. Taylor, and C.R.D. Correia J. Org. Chem. 76 2011 857
22. W.-T. Wei, J.-Y. Yeh, T.-S. Kuo, and H.-L. Wu Chem. - Eur. J. 17 2011 11405
23. L.F. Silva Jr., F.A. Siqueira, E.C. Pedrozo, F.Y.M. Vieira, and A.C. Doriguetto Org. Lett. 9 2007 1433
24. M. Kameyama, F.A. Siqueira, M. Garcia-Mijares, L.F. Silva Jr., and M.T.A. Silva Molecules 16 2011 9421
25. N.G. Nørager, L.L.R. Lorentz-Petersen, L.O. Lyngsø, J. Kehler, and K. Juhl Synlett 2011 1753
26. I.S. Kim, and Y.H. Jung Heterocycles 83 2011 2489 For recent examples, see
27. I.S. Kim, Q.R. Li, G.R. Dong, Y.C. Kim, Y.J. Hong, M. Lee, K.-W. Chi, J.S. Oh, and Y.H. Jung Eur. J. Org. Chem. 2010 1569
28. G.R. Dong, S.M. Hong, S.I. Kim, I.S. Kim, and Y.H. Jung Eur. J. Org. Chem. 2012 4200
29. S.J. Kim, T.H. Jeon, I.S. Min, I.S. Kim, and Y.H. Jung Tetrahedron Lett. 53 2012 3680
30. S.H. Lee, I.S. Kim, Q.R. Li, G.R. Dong, L.S. Jeong, and Y.H. Jung J. Org. Chem. 76 2011 10011
31. R. Rendy, Y. Zhang, A. McElrea, A. Gomez, and D.A. Klumpp J. Org. Chem. 69 2004 2340
32. For a representative submitted for publication review, see E.J. Corey, and C. Helal Angew. Chem., Int. Ed. Engl. 37 1998 1986
33. A.M. Salunkhe, and E.R. Burkhardt Tetrahedron Lett. 38 1997 1523