Summary
On the basis of an analysis of the circular dichroism and NMR spectra the absolute configuration 7R, 3R, 4S, 15S, 19S, 20S has been established for vinerine; 7S, 3R, 4S, 15S, 19S, 20S for vineridine; and 7S, 3S, 4R, 15S, 19S, 20S for N-acetylvinerine.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature cited
Sh. Z. Kasymov, P. Kh. Yuldashev, and S. Yu. Yunusov, Dokl. Akad. Nauk SSSR,162, 102 (1965).
Sh. Z. Kasymov, P. Kh. Yuldashev, and S. Yu. Yunusov, Dokl. Akad. Nauk SSSR,163, 1400 (1965).
Sh. Z. Kasymov, P. Kh. Yuldashev, and S. Yu. Yunusov, Khim. Prirodn. Soedin., 260 (1966).
H. M. McConnell, J. Chem. Phys.,27, 226 (1957).
A. D. Buckingham, Can. J. Chem.,38, 300 (1960).
R. F. Zurcher, Progr. Nucl. Magn. Res. Spectroscopy,2, Ch. 5 (1967).
C. E. Johnson and F. A. Bovey, J. Chem. Phys.,29, 1012 (1958).
B. Pullman and A. Pullman, Quantum Biochemistry, Wiley, New York (1965).
S. McLean, K. Palmer, and L. Marion, Can. J. Chem.,38, 1547 (1963).
A. M. Monro and M. J. Sewel, Tetrahedron Lett., 595 (1969).
J. B. Hendrickson and J. J. Sims, Tetrahedron Lett., 929 (1963).
A. H. Beckett, C. M. Lee, and A. W. Tackel, Tetrahedron Lett., 1709 (1963).
W. F. Trager et al. Tetrahedron,24, 523 (1968).
M. Zanger, W. W. Simons, and A. R. Gennaro, J. Org. Chem.,33, No. 9, 3673 (1968).
K. Nagarajan, M. D. Nair, and P. M. Pillai, Tetrahedron,23, 1683 (1967).
G. Fraenkele et al., J. Am. Chem. Soc.,82, 5846 (1960).
H. Spiesecke and W. G. Shneider, Tetrahedron Lett., 468 (1961).
R. A. Bell and J. K. Saunders, Can. J. Chem.,48, 1114 (1970).
N. Finch et al., J. Am. Chem. Soc.,84, 3871 (1962).
A. F. Beecham et al., Austr. J. Chem.,21, 491 (1968).
J. L. Pousset, J. Poulsson, R. J. Shine, and M. Shamma, Bull. Soc. Chim. Fr.,8, 2766 (1967).
C. Pascard-Billy, Bull. Soc. Chim. Fr.,8, 3289 (1968).
J. L. Pousset, J. Polsson, and F. Legrand, Tetrahedron Lett., 6283 (1966).
J. L. Pousset, J. Polsson, Tetrahedron Lett., 1919 (1967).
M. Shamma et al., J. Amer. Chem. Soc.,89, 1739 (1967).
E. Wenkert and N. V. Bringi, J. Amer. Chem. Soc.,81, 1474 (1959).
M. Shamma and J. M. Richey, J. Amer. Chem. Soc.,85, 2507 (1963).
G. B. Yeoh et al., Tetrahedron Lett., 931 (1966).
E. Wenkert et al ., Tetrahedron Lett., 822 (1961).
K. C. Chan, Tetrahedron Lett., 931 (1966).
Yu. Yu. Samitov, Dokl. Akad. Nauk SSSR,164, 347 (1965).
R. S. Cahn and C. K. Ingold, J. Chem. Soc., 612 (1951).
R. S. Cahn, C. K. Ingold, and V. Prelog, Angew. Chem.,5, 385 (1966).
J. W. ApSimon et al., Tetrahedron,23, 2339 (1967).
Additional information
Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 493–502, July–August, 1974.
Rights and permissions
About this article
Cite this article
Yagudaev, M.R., Malikov, V.M. & Yunusov, S.Y. Absolute configuration of vinerine and vineridine. Chem Nat Compd 10, 496–503 (1974). https://doi.org/10.1007/BF00563817
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/BF00563817