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Synthesis of polycyclic compounds related to steroids

Communication XXV. Synthesis of compounds related to estrone by the diene-condensation method

  • Organic and Biological Chemistry
  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Summary

  1. 1.

    A new method has been developed for the preparation of ethynylmagnesium bromide under pressure, and it has been condensed with aromatic and hydrogenated azomatic ketanes. In this way the synthesis has been effected in 30–46% yield of 1-methyl-1-phenyl-2-propyn-1-ol, 1-p-methoxyphenyl-1-methyl-2-propyn-1-ol, and 4-ethynyl-l,2-dihydro-7-methoxynaphthalene.

  2. 2.

    The last compound has been selectively hydrogenated to 1,2-dihydro-7-methoxy-4-vinylnaphthalene (I), which has been condensed with 2-cyclopenten-1-one (II), 2-methyl-2-cyclopenten-l-one (IX), 2,4-dimethyl-2-cylopenten-1-one (XII) and 2-cyclohexen-1-one (XVII). In this way a number of tetraeyclic ketanes related to estrone have been synthesized, and in two cases their structures have been proved.

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Authors and Affiliations

  1. Institute of Organic Chemistry of the USSR Academy of Sciences, USSR

    I. N. Nazarov & I. L. Kotlyarevsky

Authors
  1. I. N. Nazarov
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  2. I. L. Kotlyarevsky
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Nazarov, I.N., Kotlyarevsky, I.L. Synthesis of polycyclic compounds related to steroids. Russ Chem Bull 2, 977–985 (1953). https://doi.org/10.1007/BF01167545

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  • DOI: https://doi.org/10.1007/BF01167545

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