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Transformed steroids. Communication 2. Synthesis and stereochemistry of C(6)- and C(21)- fluorinated steroids

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

Summary

  1. 1.

    By the reaction of boron trifluoride etherate with 5α,6α-epoxy-17α-vinylandrostane-3β, 17β -diol 3-acetate (I) the fluorohydrin (VI) was obtained, and from this 6α-fluoro-17α-vinyltestosterone (VIII) was prepared for the first time.

  2. 2.

    The reaction of boron trifluoride etherate with the C-20 epimers of 5α,6α ∶ 20ε,21-diepoxypregnane-3β, 17β-diol (II) and (HI) gives more than one product. In both cases the main products are the monofluorohydrins (XI) and (XIII), which are formed as a result of the opening of the 5α,6α-epoxide ring.

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Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences, USSR

    A. A. Akhrem & I. G. Reshetova

Authors
  1. A. A. Akhrem
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  2. I. G. Reshetova
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Akhrem, A.A., Reshetova, I.G. Transformed steroids. Communication 2. Synthesis and stereochemistry of C(6)- and C(21)- fluorinated steroids. Russ Chem Bull 12, 102–108 (1963). https://doi.org/10.1007/BF00846958

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  • DOI: https://doi.org/10.1007/BF00846958

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