Abstract
The1H and13C chemical shifts of 11 sparteine derivatives are reported. Substituent and group effects are interpreted in terms of structural properties. The conformational equilibrium of aphyllin is determined.
Similar content being viewed by others
References
M. F. Grundon, Nat. Prod. Rep.,1, 349 (1984).
R. B. Herbert, Nat. Prod. Rep.,3, 185 (1986).
M. F. Grundon, Nat. Proc. Rep.,4, 415 (1987).
R. B. Herbert, Nat. Prod. Rep.,4, 423 (1987).
R. B. Herbert, Nat. Prod. Rep.,5, 523 (1988).
M. F. Grundon, Nat. Prod. Rep.,6, 523 (1989).
J. P. Michael, Nat. Proc. Rep.,7, 485 (1990).
J. P. Michael, Nat. Prod. Rep.,8, 553 (1991).
R. B. Herbert, Nat. Prod. Rep.,10, 575 (1993).
M. Wink, Planta Med.,53, 509 (1987).
M. Wink, Insect Plant Interactions, Vol. 4, E. A. Bernays (ed.), Boca Raton, Fl.: CRS Press (1992), p. 133.
M. Wink, Lupinen, 1991: Forschung, Anbau und Verwertung., Universitat Heidelberg (1992).
F. Bohlmann and R. Zeisberg, Chem. Ber.,108, 1043 (1975).
A. S. Sadykov, F. G. Kamayev, V. A. Korenevsky, V. B. Leont'ev, and Yu. A. Ustynyuk, Org. Magn. Reson.,4, 837 (1972).
A. Katrusiak, Z. Kaluski, H. Podkowinska, and J. Skolik, J. Crystallog. Spectrosc. Res.,17, 259 (1987).
A. Katrusiak, Z. Kaluski, P. Pietrzak, and J. Skolik, J. Crystallog. Spectrosc. Res.,16, 191, 775, 879 (1986).
A. Katrusiak, Z. Kaluski, P. Pietrzak, and J. Skolik, J. Crystallog. Spectrosc. Res.,13, 151 (1983).
A. Katrusiak, Z. Kaluski, P. Pietrzak, and J. Sholik, J. Crystallog. Spectrosc. Res.,17, 13 (1987).
J. Rana and D. J. Robins, J. Chem. Soc. Perkin Trans. I, No. 6, 1133 (1986).
W. Boczon, J. Skolik, and B. Koziol, J. Mol. Struct.,328, 1 (1994).
J. Skolik, W. Boczon, and R. Koziol, J. Mol. Struct.,328, 11 (1994).
A. Katrusiak, Z. Kaluski, P. Pietrzak, and J. Skolik, J. Crystallog. Spectrosc. Res.,16, 5 (1986).
A. Katrusiak, Z. Kaluski, P. Pietrzak, and J. Skolik, J. Crystallog. Spectrosc. Res.,17, 1 (1987).
U. Majchrzak-Kuczynska and J. Skolik, unpublished results.
A. Katrusiak, Z. Kaluski, P. Pietrzak, and J. Skolik, J. Crystallogr. Spectrosc. Res.,13, 2 (1983).
A. J. Shaka and R. Freeman, J. Magn. Reson.,52, 502 (1982).
W. M. Golembiewski, Magn. Reson. Chem.,24, 105 (1986).
M. F. Simeonov, S. L. Spassov, H. Duddeck, U. Majchrzak-Kuczynska, and J. Skolik, Magn. Reson. Chem.,27, 476 (1989).
P. Mascagni, W. A. Gibbons, K. Asres, J. D. Phillipson, and N. Niccolai, Tetrahedron,43, 1149 (1987).
D. S. Rycroft, D. J. Robins, and I. H. Sadler, Magn. Reson. Chem.,29, 936 (1991).
N. J. Leonard, P. D. Thomas, and P. D. Gash, J. Am. Chem. Soc.,77, 1552 (1955).
K. Langowska, J. Skolik, and M. Wiewiorowski, Bull. Acad. Pol. Chim.,25, 11 (1977).
U. Majchrzak-Kuczynska, A. E. Koziol, and M. Wiewiorowski, J. Mol. Struct.,160, 189 (1987).
U. Majchrzak-Kuczynska, Ph. D., Thesis, Poznan, Poland: A. Mickiewicz University (1981).
M. D. Bratek and M. Wiewiorowski, Roczn. Chem.,33, 1187 (1959).
M. Markiewicz, Ph. D., Thesis, Poznan, Poland: A. Mickiewicz University (1980).
O. E. Edwards and F. H. Clark, Can. J. Chem.,32, 235 (1954).
P. Pietrzak, Ph. D., Thesis, Poznan, Poland: A. Mickiewicz University (1984).
P. Pietrzak and J. Skolik, Zesz. Nauk. Wyzsza Szk. Ekon. Poznan. Ser. I., No. 112, 101 (1984).
J. Skolik, Zesz Nauk. Wyzsza Szk. Ekon. Poznan, Ser. I., No. 53, 165 (1974).
M. Wiewiorowski, O. E. Edwards, and M. D. Bratek-Wiewiorowska, Can. J. Chem.,45, 1447 (1967).
H. Duddeck and W. Dietrich, Structure Elucidation by Modern NMR, A Workbook, 2nd edn., N.Y.:SteinkopfSpringer (1992).
W. R. Croasmun and R. M. K. Carlson, Two-Dimensional NMR Spectroscopy. Applications for Chemists and Biochemists, 2nd edn., N.Y.: VCH Publishers (1994).
L. P. Lindeman and J. Q. Adams, Anal. Chem.,43, 1245 (1971).
H. Duddeck, Top. Stereochem.,16, 219 (1986).
D. M. Grant and B. V. Cheney, J. Am. Chem. Soc.,89, 5315 (1967).
B. V. Cheney and D. M. Grant, J. Am. Chem. Soc.,89, 5319 (1967).
N. K. Wilson and J. B. Stothers, Top. Stereochem.,8, 1 (1974).
W. A. Ayer, L. M. Browne, S. Fung, and J. B. Stothers, Org. Magn. Reson.,11, 73 (1978).
Additional information
Dedicated to Prof. N. S. Zefirov on the occasion of his 60th birthday.
Ruhr-Universität Bochum, Fakultät für Chemie, Bochum, Germany. Universität Hannover, Institut für Organische Chemie, Hannover, Germany (present address). Department of Organic Chemistry, Poznan Academy of Economics, Poznan, Poland. Published in Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1026–1033, August, 1995. Original article submitted May 10, 1995.
Rights and permissions
About this article
Cite this article
Duddeck, H., Skolik, J. & Majchrzak-Kuczynska, U. Tetracyclic alkaloids of the sparteine group.1H and13C NMR spectroscopy and conformational analysis. Chem Heterocycl Compd 31, 893–899 (1995). https://doi.org/10.1007/BF01170317
Issue Date:
DOI: https://doi.org/10.1007/BF01170317