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Phytoestrogens

I. Syntheses among coumestan derivatives: 8, 13-diallylcoumestrol

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Chemistry of Natural Compounds Aims and scope

Summary

A new method for the production of ω-(2, 4-dimethoxyphenyl)-resacetophenone, the basic intermediate in the synthesis of the phytoestrogen coumestrol by Emerson and Bickoff's method, has been described. The new variant of the production of this substance shortens the synthesis of coumestrol by a factor of 2. 7, 12-Diallyloxycoumestrol has been isomerized by a Claisen rearrangement into 8, 13-diallylcoumestrol.

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References

  1. A. A. Shamshurin, ZhVKhO, 8, 260, 1963.

    Google Scholar 

  2. E. M. Bickoff, A. N. Booth, and R. L. Lyman, Sci., 126, 969, 1957; E. M. Bickoff, R. L. Lyman, A. L. Livingston, and A. N. Booth, J. Am. Chem. Soc., 80, 3969, 1958.

    Article  CAS  Google Scholar 

  3. A. L. Livingston, E. M. Bickoff, R. E. Lundin, and L. Lurd, Tetrah., 20, 1963, 1964.

    Article  CAS  Google Scholar 

  4. Angew. Chem., 76, no. 12, 244, 1964; Abstracts 147, Meeting der Am. Chem. Soc., 3, A, 1964.

  5. C. Deschamps-Vallet and C. Mentzer, C. R., 251, 736, 1960.

    CAS  Google Scholar 

  6. U. S. Pat. No. 2 884 427, 1959.

  7. E. Kaiser, Angew. Chem., 72, 715, 1960.

    Google Scholar 

  8. A. A. Shamshurin, ZhOKh, 14, 211, 1941.

    Google Scholar 

  9. O. H. Emerson and E. M. Bickoff, J. Am. Chem. Soc., 80, 4381, 1958.

    Article  CAS  Google Scholar 

  10. Yoshiyuki Kawase, Bull. Chem. Soc., Japan, 32, 690, 1959.

    Article  Google Scholar 

  11. Mitter and Maitra, J. Ind. Chem. Soc., 13, 236, 1936.

    CAS  Google Scholar 

  12. B. Reichert and W. Koch, Arch. Pharm., 273, 265, 1935.

    Article  CAS  Google Scholar 

  13. A. A. Shamshurin and M. A. Yampol'skaya, Author's Certificate No. 165700, Byull. izobret., no. 20, 12, 1964.

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Khimiya Prirodnykh Soedinenii, Vol. 2, No. 1, pp. 51–55, 1966

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Shamshurin, A.A., Yampol'skaya, M.A. & Simonova, L.L. Phytoestrogens. Chem Nat Compd 2, 42–45 (1966). https://doi.org/10.1007/BF00566600

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  • DOI: https://doi.org/10.1007/BF00566600

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