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The structure of fetidine

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Summary

Fetidine is a binary aporphine-benzyltetrahydroisoquinoline alkaloid. A structural formula for fetidine has been proposed on the basis of the isolation of (+)-laudanosine (IIIa) and (+)-isoboldine (IV) from the degradation of fetidine (I) with sodium in liquid ammonia.

The obtaining of (+)-laudanosine and (+)-glaucine has established the absolute configuration of the two asymmetric centers of fetidine.

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References

  1. Dzh. Sargazakov, Z. F. Ismailov, and S. Yu. Yunusov, DAN UzSSR, no. 6, 28, 1963.

  2. S. Yu. Yunusov, R. A. Konovalova, and A. P. Orekhov, ZhOKh, 10, 64, 1940.

    Google Scholar 

  3. A. Pictet and B. Anthanasescu, Ber., 33, 2346, 1900.

    CAS  Google Scholar 

  4. E. Spath and E. Bernhauer, Ber., 58, 200, 1925.

    Google Scholar 

  5. M. Tomita and D. Kunimoto, J. Pharmac. Soc. Japan, vol. 81, no. 1, pp. 113–115, 1961; vol. 82, no. 5, pp. 734–741, 1962.

    CAS  Google Scholar 

  6. M. Shamma and A. Slusarchyk, Chem. Rev., 64, 59, 1964.

    Article  CAS  Google Scholar 

  7. Ya. V. Rashkes, ZhAKh, 20, 238, 1965.

    CAS  Google Scholar 

  8. H. Chikainatsu, M. Tomita, and M. Kotake, J. Chem. Soc. Japan, vol. 82, no. 12, pp. 1708–1712, 1961.

    Google Scholar 

  9. P. S. Clezy, A. W. Nichol, and E. Gellert, Exper., 19, 1, 1963.

    Article  CAS  Google Scholar 

  10. R. Tschesche, P. Weizel, R. Moll, and G. Legler, Tetrah., 20, 1435, 1964.

    Article  CAS  Google Scholar 

  11. E. Späth and K. Tharrer, Ber., 66, 904, 1933.

    Google Scholar 

  12. S. Yu. Yunusov, Jubilee Collection of AS UzSSR Dedicated to the 25th Anniversary of UzSSR [in Russian], Tashkent, 233, 1949.

  13. H. Corrodi and E. Hardegger, Helv. Chim. Acta, 39, 889, 1956; A. R. Battersby et al., J. Chem. Soc., 2239, 1965.

    Article  CAS  Google Scholar 

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Khimiya Prirodnykh Soedinenii, Vol. 2, No. 1, pp. 43–48, 1966

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Ismailov, Z.F., Yunusov, S.Y. The structure of fetidine. Chem Nat Compd 2, 35–39 (1966). https://doi.org/10.1007/BF00566598

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  • DOI: https://doi.org/10.1007/BF00566598

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