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A study of the structure and stereochemistry of ungernia alkaloids by NMR spectroscopy

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Conclusions

1. In a study of the NMR spectra of ungerine, dihydroungerine, hippeastrine, hippeastrine acetate, dihydrohippeastrine, dihydrohippeastrine acetate, and unsevine it has been shown that the B and C rings in these compounds have a cis linkage.

2. It has been found that, in contrast to the alkaloid clivonine, in dihydrohippeastrine the B/C ring-linkage is cis, and the N-CH3 group is located above the plane of the benzene ring.

3. The orientations of the H5, H5a, and H11b protons and the substituent OR at C5 of ring C have been established.

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References

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    M. R. Yagudaev, Kh. A. Abduazimov, and S. Yu. Yunusov, KhPS [Chemistry of Natural Compounds], 5, 99, 1969.

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    S. L. Portnova, Yu. N. Sheinker, A. A. Akhrem, A. M. Prokhoda, and A. V. Kamernitskii, ZhOrKh, 3, 44, 1967.

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    W. A. Hawksworth, P. W. Jeffs, B. K. Tidd, and T. P. Toube, J. Chem. Soc., 1991, 1965.

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    W. Döpke, M. Bienert, P. W. Jeffs, and D. S. Farrier, Tetrah. Let., no. 5, 451, 1967.

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Additional information

Khimiya Prirodnykh Soedinenii, Vol. 6, No. 1, pp. 94–97, 1970

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Yagudaev, M.R., Abduazimov, K.A. & Yunusov, S.Y. A study of the structure and stereochemistry of ungernia alkaloids by NMR spectroscopy. Chem Nat Compd 6, 88–91 (1970). https://doi.org/10.1007/BF00564166

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Keywords

  • Lactone Carbonyl
  • Methylenedioxy Group
  • Stereochemical Feature
  • Double Resonance Method
  • Hippeastrine