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Russian Chemical Bulletin

, Volume 67, Issue 11, pp 2112–2120 | Cite as

An efficient synthesis of 3-methoxy-19-norpregna-1,3,5(10),16-tetraen-20-one

  • Yu. V. KuznetsovEmail author
  • I. S. Levina
  • A. S. Shashkov
  • I. V. Zavarzin
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Abstract

An efficient preparative method for the synthesis of 3-methoxy-19-norpregna-1,3,5(10), 16-tetraen-20-one was suggested. This compound is a key intermediate product in the preparation of 3,20-dihydroxy-19-norpregnatrienes, antagonists of estrogen receptor and cytotoxic agents. The reaction of 16-dehydro-17-carbonitrile (obtained in two steps from estrone methyl ether) with methyl magnesium halides gave the target product in high yield. While studying this reaction, we isolated and characterized an unusual steroid dimer, a fused 16,17-pyridinosteroid substituted in the hetero ring of the second steroid molecule. A mechanism of its formation was suggested.

Key words

antiestrogens Grignard reagent steroid dimer NMR spectroscopy X-ray diffraction pregnatetraene 

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • Yu. V. Kuznetsov
    • 1
    Email author
  • I. S. Levina
    • 1
  • A. S. Shashkov
    • 1
  • I. V. Zavarzin
    • 1
  1. 1.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation

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