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New synthesis of estradiol from androsta-1,4-diene-3,17-dione

  • Chemistry of Natural Compounds and Bioorganic Chemistry
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Russian Chemical Bulletin Aims and scope

Abstract

A new method for the aromatization of ring A in androsta-1,4-diene-3,17-dione, available from sterols by means of the microbiological degradation of the side chain, was developed. The method consists of the reduction of androsta-1,4-diene-3,17-dione to the corresponding dienediol followed by double C,O-deprotonation of ring A, accompanied by expulsion of the 19-methyl group and formation of estradiol in a high yield.

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References

  1. L. F. Fieser and M. Fieser,Steroids Reinhold Publishing Corporation, New York, 1959.

    Google Scholar 

  2. FRG Pat 2,537,254;Chem. Abstrs., 1976,85, 94609; FRG Pat. 3,931,820;Chem. Abstrs., 1991,115, 29716.

    Google Scholar 

  3. H. L. Dryden, G. M. Webber, and J. Weiczorek,J. Am. Chem. Soc., 1964,86, 742.

    Article  CAS  Google Scholar 

  4. V. I. Mel'nikova and K. K. Pivnitsky,Zh. Org. Khim., 1972,8, 68 [J. Org. Chem., 1972,8 (Engl. Transl.)].

    Google Scholar 

  5. M. J. Gentles, J. B. Moss, H. L. Herzog, and E. B. Hershberg,J. Am. Chem. Soc., 1958,80, 3702.

    Article  CAS  Google Scholar 

  6. H. C. Brown and A. Tsukamoto,J. Am. Chem. Soc. 1959,81, 502;J. Am. Chem. Soc., 1964,86, 1079.

    Article  CAS  Google Scholar 

  7. H. C. Brown and N. M. Yoon,J. Am. Chem. Soc., 1966, 88, 1464.

    Article  CAS  Google Scholar 

  8. A. Hajos,Komplexe Hydride, VEB Deutscher Verlag der Wissenschaften, Berlin, 1966.

    Google Scholar 

  9. The Merck Index, 9th ed., Ed. M. Windholz, Merck and Co., Inc., New York, 1976, 485 pp.

    Google Scholar 

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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 599–601, March, 1999.

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Vasiljeva, L.L., Demin, P.M., Kochev, D.M. et al. New synthesis of estradiol from androsta-1,4-diene-3,17-dione. Russ Chem Bull 48, 593–595 (1999). https://doi.org/10.1007/BF02496187

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  • DOI: https://doi.org/10.1007/BF02496187

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