Pictet-Spengler reaction of biogenic amines with (2R)-N- glyoxyloylbornane-10,2-sultam. Enantioselective synthesis of (S)-(+)-N- methylcalycotomine and (R)-(+)-xylopinine

Heterocycles

Volumn 51, Issue 12, 1999, Pages 2871-2879

  Czarnocki, Zbigniew ^a   Araźny, Zbigniew ^a  

^a UNIVERSITY OF WARSAW   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

BIOGENIC AMINE; BORNANE DERIVATIVE; XYLOPININE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; ENANTIOMER; POLYMERIZATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0343986494     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-99-8681     Document Type: Article

References (21)

1. A. Pictet and T. Spengler, Ber., 1911, 44, 2030.
2. W. M. Whaley and T. R. Govindachari, Org. React., 1951, 6, 151.
3. M. Shamma and J. L. Moniot, In 'Isoquinoline Alkaloids Research, 1972-1977', Plenum Press, New York, 1978, Chapter 1.
4. E. D. Cox, L. K. Hamaker, J. Li, P, Yu, M. Czerwinski, L. Deng, D.W. Bennett, J. Cook, W. H. Watson, and M. Krawiec, J. Org. Chem., 1997, 62, 44, and references therein.
5. P. Bravo, M. Crucianelli, A. Farina, S. V. Meille, A. Volonterio, and M. Zanda, Eur. J. Org. Chem., 1998, 3, 435.
6. P. R. R. Costa, L. M. Cabral, K. G. Alencar, L. L. Schmidt, and M. L. L. A. Vasconcellos, Tetrahedron Lett., 1997, 7021.
7. G. Schmidt, H. Waldmann, H. Henke, and M. Burkard, Chem. Eur-J., 1996, 2, 1566.
8. W. M. Dai, H. J. Zhu, and X. J. Hao, Tetrahedron Lett., 1996, 37, 5971.
9. E. J. Corey and D. Y. Gin, Tetrahedron Lett., 1996, 37, 7163.
10. I. M. Piper, D. B. MacLean, I. Kvarnström, and W. A. Szarek, Can. J. Chem., 1983, 61, 2721.
11. Z. Czarnocki, D. Suh, D. B. MacLean, P. G. Hultin, and W. A. Szarek, Can. J. Chem., 1992, 70, 1555.
12. Z. Czarnocki, J. B. Mieczkowski, J. Kiegiel, and Z. Araźny, Tetrahedron: Asymmetry, 1995, 6, 2899.
13. W. Oppolzer, Pure Appl. Chem., 1990, 43, 1969 and references cited therein.
14. T. Bauer, C. Chapuis, J. Kozak, and J. Jurczak, Helv. Chim. Acta, 1989, 72, 482.
15. P. Kerekes, N. Padam Sharma, A. Brossi, and J. L. McLaughlin, J. Nat. Prod., 1985, 48, 142.
16. Z. Czarnocki, D. B. MacLean, and W. A. Szarek, Can. J. Chem., 1986, 64, 2205.
17. Z. Czarnocki, D. B. MacLean, and W. A. Szarek, Bull. Soc. Chim. Belg., 1986, 95, 749.
18. Z. Czarnocki, J. Chem. Res. (M), 1992, 2801.
19. W. Rossouw, A. F. Hundt, J. A. Steenkamp, and D. Ferreira, Tetrahedron, 1994, 50, 12477.
20. E. Hardegger and H. Corrodi, Helv. Chim. Acta, 1956, 39, 889.
21. M. J. Munchhof and A. I. Meyers, J. Org. Chem., 1996, 61, 4607.