Enantioselective synthesis of some tetrahydroisoquinoline and tetrahydro-β-carboline alkaloids

Tetrahedron Asymmetry

Volumn 18, Issue 3, 2007, Pages 406-413

  Szawkało, Joanna ^a   Czarnocki, Stefan J ^a   Zawadzka, Anna ^a   Wojtasiewicz, Krystyna ^a   Leniewski, Andrzej ^a   Maurin, Jan K ^b,c   Czarnocki, Zbigniew ^a   Drabowicz, Józef ^d  

^a UNIVERSITY OF WARSAW   (Poland)

^b NATIONAL MEDICINES INSTITUTE   (Poland)

^c INSTITUTE OF ATOMIC ENERGY   (Poland)

^d CENTRE OF MOLECULAR AND MACROMOLECULAR STUDIES   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID DERIVATIVE; CARBOLINE DERIVATIVE; CRYSPINE A; DESBROMOARBORESCIDINE; HARMICINE; OCTAHYDROINDOLO[2,3 A]QUINOLIZIDINE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; ENANTIOSELECTIVITY; HYDROGENATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 33847641077     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2007.01.014     Document Type: Article

References (57)

1. Palmer M.J., and Wills M. Tetrahedron: Asymmetry 10 (1999) 2045-2061
2. Clapham S.E., Hadzovic A., and Morris R.H. Coord. Chem. Rev. 248 (2004) 2201-2237
3. Gladiali S., and Alberico E. Chem. Soc. Rev. 35 (2006) 226-236
4. Yurovskaya M.A., and Karchava A.V. Tetrahedron: Asymmetry 9 (1998) 3331-3352
5. Zassinovich G., Mestroni G., and Gladiali S. Chem. Rev. 92 (1992) 1051-1069
6. Yamakawa M., Yamada I., and Noyori R. Angew. Chem., Int. Ed. 40 (2001) 2818-2821
7. Hamada T., Torii T., Izawa K., Noyori R., and Ikariya T. Org. Lett. 4 (2002) 4373-4376
8. Nishibayashi Y., Takei I., Uemura S., and Hidai M. Organometallics 18 (1999) 2291-2293
9. Kawamoto A., and Wills M. Tetrahedron: Asymmetry 11 (2000) 3257-3261
10. Yamashita H., Ohtani T., Morita S., Otsubo K., Kan K., Matsubara J., Kitano K., Kawano Y., Uchiba M., and Tabusa F. Heterocycles 56 (2002) 123-128
11. Bianchini C., Glendenning L., Zanobini F., Farnetti E., Graziani M., and Nagy E. J. Mol. Catal. A: Chem. 132 (1998) 13-19
12. Yim A.S.Y., and Wills M. Tetrahedron 61 (2005) 7994-8004
13. Wang Z., Ye X., Wei S., Wu P., Zhang A., and Sun J. Org. Lett. 8 (2006) 999-1001
14. Williams G.D., Wade C.E., and Wills M. Chem. Commun. (2005) 4735-4737
15. Uematsu N., Fujii A., Hashiguchi S., Ikariya T., and Noyori R. J. Am. Chem. Soc. 118 (1996) 4916-4917
16. Mao J., and Baker D.C. Org. Lett. 1 (1999) 841-843
17. Santos L.S., Pilli R.A., and Rawal V.H. J. Org. Chem. 69 (2004) 1283-1289
18. Kaldor I., Feldman P.L., Mook R.A., Ray J.A., Samano V., Sefler A.M., Thompson J.B., Travis B.R., and Boros E.E. J. Org. Chem. 66 (2001) 3495-3501
19. Samano V., Ray A.J., Thomson J.B., Mook R.A., Jung D.K., Koble C.S., Martin M.T., Bigham E.C., Regitz C.S., Feldman P.L., and Boros E.E. Org. Lett. 1 (1999) 1993-1996
20. Tietze L.F., Rackelmann N., and Muller I. Chem. Eur. J. 10 (2004) 2722-2731
21. Santos L.S., Pilli R.A., and Rawal V.H. J. Org. Chem. 69 (2004) 1283-1289
22. Vedejs E., Trapencieris P., and Suna E. J. Org. Chem. 64 (1999) 6724-6729
23. Meuzelaar G.J., van Vliet M.C.A., Maat L., and Sheldon R.A. Eur. J. Org. Chem. (1999) 2315-2321
24. Ahn K.H., Ham C., Kim S.K., and Cho C.W. J. Org. Chem. 62 (1997) 7047-7048
25. Ahn K.H., Ham C., and Kim S.K. Tetrahedron Lett. 39 (1998) 6321-6322
26. Tietze L.F., Zhou Y., and Topken E. Eur. J. Org. Chem. (2000) 2247-2252
27. Mao J., and Baker D.C. Org. Lett. 1 (1999) 841-843
28. Hannedouche J., Clarkon G.J., and Wills M. J. Am. Chem. Soc. 126 (2004) 986-987
29. Roszkowski P., Wojtasiewicz K., Leniewski A., Maurin J.K., Lis T., and Czarnocki Z. J. Mol. Catal. A: Chem. 232 (2005) 143-149
30. Roszkowski P., Maurin J.K., and Czarnocki Z. Tetrahedron: Asymmetry 17 (2006) 1415-1419
31. Szawkało J., Zawadzka A., Wojtasiewicz K., Leniewski A., Drabowicz J., and Czarnocki Z. Tetrahedron: Asymmetry 16 (2005) 3619-3621
32. Zhang Q., Tu G., Zhao Y., and Cheng T. Tetrahedron 58 (2002) 6795-6798
33. Xie W.D., Li P.L., and Jia Z.J. Pharmazie 60 (2005) 233-236
34. Curzons A.D., Constable D.J.C., Mortimer D.N., and Cunningham V.L. Green Chem. 3 (2001) 1-6
35. European Pharmacopoeia, 3rd Ed. Supplement, 2000; pp 851-852.
36. Bansal D., Malla N., and Mahajan R.C. Indian J. Med. Res. 123 (2006) 115-118
37. Zhou Y.D., Kim Y.P., Mohammed K.A., Jones D.K., Muhammad I., Dunbar D.C., and Nagle D.G. J. Nat. Prod. 68 (2005) 847-950
38. Garcia E., Lete E., and Sotomayor N. J. Org. Chem. 71 (2006) 6776-6784
39. Zymalkowski F., and Schmidt F. Arch. Pharm. 3 (1967) 229-233
40. Kam T.-S., and Sim K.-M. Phytochemistry 47 (1998) 145-147
41. Knolker H.J., and Agarwal S. Synlett 10 (2004) 1767-1768
42. Itoh T., Miyazkaki M., Nagata K., Nakamura S., and Ohsawa A. Heterocycles 63 (2004) 655-661
43. McLean S., Dmitrienko G.I., and Szakolcai A. Can. J. Chem. 54 (1976) 1262-1277
44. Fujii T., Ohba M., and Ohashi T. Tetrahedron 49 (1993) 1879-1890
45. Dolby L.J., and Gribble G.W. J. Org. Chem. 32 (1967) 1391-1398
46. Schut R.N., and Leipzig T.J. J. Het. Chem. 3 (1966) 101-102
47. Nakagawa M., Kiuchi M., Obi M., Tonozuka M., Kobayashi K., Hino T., and Ban Y. Chem. Pharm. Bull. 23 (1975) 304-312
48. Gribble G.W. In: Atta ur-Ramman (Ed). Stereoselective Synthesis, Part A; Studies in Natural Products Vol. I (1988), Elsevier 123-162
49. Fanso-Free S.N.Y., Furst G.T., Srinivasan P.R., Lichter R.L., Nelson R.B., Panetta J.A., and Gribble G.W. J. Am. Chem. Soc. 101 (1979) 1549-1553
50. Santos L.S., Pilli R.A., and Rawal V.H. J. Org. Chem. 69 (2004) 1283-1289
51. Johns S.R., Lamberton J.A., and Occolowitz J.L. Aust. J. Chem. 19 (1966) 1951-1954
52. Allin S.M., Thomas C.I., Allard J.E., Doyle K., and Elsegood M.R.J. Eur. J. Org. Chem. (2005) 4179-4186
53. Sheldrick G.M. Acta Crystallogr. A 46 (1990) 467-473
54. Sheldrick G.M. shelxl-97 Program for X-ray Structure Refinement (1997), University of Göttingen, Germany
55. Flack H.D. Acta Crystallogr. A 39 (1983) 876-881
56. Bremner J.B., and Winzenberg K.N. Aust. J. Chem. 38 (1985) 1591-1612
57. Ashcroft W.R., Martinez S.J., and Joule J.A. Tetrahedron 37 (1981) 3005-3007