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Cyclization of 3-methoxy-8, 14-seco-D-homoestra-1, 3, 5(10), 9(11)-tetraene-14, 17a-dione into D-homoestrone derivatives

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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

In the cyclization of 3-methoxy-8, 14-seco-D-homoestra-1,3,5,(10),9(11)-tetraene-14, 17a-dione (I) the stereoisomeric 14α-hydroxy-3-methoxy-D-homoestra-1,3,5(10),9(11)-tetraen-17a-ones (III) and (IV) are formed at first, and after dehydration and isomerization these are converted into 3-methoxy-D-homoestra-1,3,5(10),8,14-pentaen-17a-one (II). The ketol (IV) is much more readily dehydrated than the ketol (III) and is probably themain intermediate product in the cyclization of the diketone (I).

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Literature cited

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Authors and Affiliations

  1. Institute for the Chemistry of Natural Products, Academy of Sciences, USSR

    A. V. Zakharychev, S. N. Ananchenko & I. V. Torgov

Authors
  1. A. V. Zakharychev
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  2. S. N. Ananchenko
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  3. I. V. Torgov
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Additional information

Translated from Izvestiya Akadeemii Nauk SSSR, Seriya Khimicheskaya, No. 8, pp. 1413–1416, August, 1965 Original article submitted June 24, 1963

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Zakharychev, A.V., Ananchenko, S.N. & Torgov, I.V. Cyclization of 3-methoxy-8, 14-seco-D-homoestra-1, 3, 5(10), 9(11)-tetraene-14, 17a-dione into D-homoestrone derivatives. Russ Chem Bull 14, 1373–1375 (1965). https://doi.org/10.1007/BF00846195

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  • DOI: https://doi.org/10.1007/BF00846195

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