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Synthesis of E- and Z-isomeric progesterone 3-O-methyloximes

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Abstract

Isomeric E- and Z-3-methoxyiminopregn-4-en-20-ones were obtained from progesterone by selective ketalization of 20-oxo group, subsequent oximation of the remaining 3-keto group, removal of the protecting group, and chromatographic separation of isomers.

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References

  1. K. P. Madauss, E. L. Stewart, Sh. P. Williams, Med. Res. Rev., 2007, 27, 374.

    Article  CAS  Google Scholar 

  2. P. Thomas. Gen. Comp. Endocrinol., 2012, 175, 367.

    Article  CAS  Google Scholar 

  3. M. Luconi, F. Francavilla, I. Porazzi, B. Macerola, G. Forti, E. Baldi, Steroids, 2004, 69, 553.

    Article  CAS  Google Scholar 

  4. N. K. Evanson, J. P. Herman, R. R. Sakai, E. G. Krause, J. Neuroendocrinol., 2010, 22, 846.

    CAS  Google Scholar 

  5. Y. Zhu, J. Bond, P. Thomas. Proc. Natl. Acad. Sci. USA, 2003, 100, 2237.

    Article  CAS  Google Scholar 

  6. G. E. Dressing, J. E. Goldberg, N. J. Charles, K. L. Schwertfeger, C. A. Lange, Steroids, 2011, 76, 11.

    Article  CAS  Google Scholar 

  7. O. V. Lisanova, T. A. Shchelkunova, I. A. Morozov, P. M. Rubtsov, I. S. Levina, L. E. Kulikova, A. N. Smirnov, Biochemistry (Moscow) (Engl. Transl.), 2013, 78, 236 [Biokhim., 2013, 78 (6), 320].

    Article  CAS  Google Scholar 

  8. D. Enders, B. E. Rendenbath, Tetrahedron, 1986, 42, 2235.

    Article  CAS  Google Scholar 

  9. A. Szentezi, A. Gergely, P. Horvath, S. Maho, P. Matyus, Gy. Szasz, Curr. Med. Chem., 2001, 8, 1341.

    Article  Google Scholar 

  10. Ch. J. MacNevin, F. Atif, I. Sayeed, D. G. Stein, D. C. Liotta, J. Med. Chem., 2009, 52, 6012.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    V. A. Zolottsev, I. V. Zavarzin, V. Z. Shirinyan & I. S. Levina

Authors
  1. V. A. Zolottsev
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  2. I. V. Zavarzin
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  3. V. Z. Shirinyan
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  4. I. S. Levina
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Corresponding author

Correspondence to I. S. Levina.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 2086–2087, September, 2013.

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Zolottsev, V.A., Zavarzin, I.V., Shirinyan, V.Z. et al. Synthesis of E- and Z-isomeric progesterone 3-O-methyloximes. Russ Chem Bull 62, 2086–2087 (2013). https://doi.org/10.1007/s11172-013-0303-y

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  • DOI: https://doi.org/10.1007/s11172-013-0303-y

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