An NMR and molecular mechanics structural study on some ethereal and Δ3,10 isomers of cinchona alkaloids

Journal of Molecular Structure

Volumn 405, Issue 2-3, 1997, Pages 219-230

  Thiel, Jacek ^a   Fiedorow, Piotr ^a  

^a ADAM MICKIEWICZ UNIVERSITY   (Poland)

Author keywords

Cinchona alkaloid; Conformational isomerism; Molecular mechanics; NMR spectroscopy

Indexed keywords

EID: 0030954981     PISSN: 00222860     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-2860(96)09599-3     Document Type: Article

References (25)

1. T.A. Henry, The Plant Alkaloids, 4th edn., Churchill, London, 1949, pp. 448-454.
2. R.B. Turner and R.B. Woodward, in R.H.F. Manske (Ed.), The Alkaloids, Vol. 3, Academic Press, New York, 1953, Chapter 16, pp. 20, 21.
3. E.M. Gibbs and T.A. Henry, J. Chem. Soc., (1939) 240.
4. W. Solomon, J. Chem Soc., (1941) 77.
5. J. Suszko and J. Thiel, Roczniki Chem., 49 (1975) 47.
6. E. Jungfleisch and E. Leger, Ann. Chim., 14 (1920) 59.
7. J. Thiel, J. Mol. Struct., 319 (1994) 153.
8. Z. Dega-Szafran, Bull. Acad. Polon. Sci., Ser. Sci. Chim. 14 (1966) 523.
9. Z. Dega-Szafran and W. Mitura, Bull. Acad. Polon. Sci., Ser. Sci. Chim., 13 (1965) 591.
10. G.G. Lyle and L.K. Keefer, Tetrahedron, 23 (1967) 3253.
11. J. Suszko and J. Thiel, Roczniki Chem., 48 (1974) 1281.
12. T. Dubas, A. Konopnicki and J. Suszko, Roczniki Chem., 13 (1933) 464.
13. T. Domanski and J. Suszko, Rec. Trav. Chim. Pay-Bas, 54 (1935) 481.
14. G.D.H. Dijkstra, R.M. Kellog, H. Wynberg, J.S. Svendsen, I. Marko and K.B. Sharpless, J. Am. Chem. Soc., 111 (1989) 8069.
15. C.G. Moreland, A. Philip and F.I. Carrol, J. Org. Chem. 33 (1974) 2413.
16. R. Verpoorte, J. Schripsema and T. van der Leer Cinchona alkaloids, in A. Brossi (Ed.), The Alkaloids - Chemistry and Pharmacology, Vol. 34, Academic Press, San Diego, 1988, Chapter 6. p. 360.
17. O. Prakash, R. Roy, I.P. Singh, R. Pratap, S.P. Popli and D.S. Bhakuni, Indian J. Chem., 27B (1988) 950.
18. F.I. Carrol, P. Abraham, K. Gaetano, S.W. Mascarella, R.A. Wohl, J. Lind and K. Petzoldt, J. Chem. Soc. Perkin Trans. I: (1991) 3017.
19. E. Lipmaa, T. Pehk, J. Paassivirta, N. Belikova and A. Plate, Org. Magn. Reson., 2 (1970) 581.
20. G. van Binst and D. Tourwe, Org. Magn. Reson., 4 (1972) 625.
21. E.L. Eliel and S.H. Wilen, with a contribution by L.N. Mander, Stereochemistry of Organic Compounds, J. Wiley, New York, 1994, Chapter 11, p. 764.
22. F.W. Wehrli and T. Wirthlin, Interpretation of Carbon-13 NMR Spectra, Heyden, London, 1976. Chapter 2, pp. 38, 45.
23. C.A.G. Haasnoot, F.A.M. de Leeuw and C. Altona, Tetrahedron, 36 (1980) 2783.
24. U. Berg, M. Aune and O. Matson, Tetrahedron Lett., 36 (1995) 2137.
25. G.D.H. Dijkstra, R.M. Kellog and H. Wynberg, J. Org. Chem., 55 (1990) 6121.