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Steroids

XXXVI. The opening of an epoxide ring with organometallic compounds

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Chemistry of Natural Compounds Aims and scope

Conclusions

The opening of the epoxide ring of the 3,20-diketal of 16α, 17α-epoxy-Δ5-pregnene-3, 20-dione and of the acetate of the 20-ketal of 16α, 17α-epoxy-Δ5-pregnene-3β-ol-20-one with methyllithium has been studied. It was found that no products of the nucleophilic addition of methyllithium to the epoxide ring are formed, and after deketalization, 16-methyl-Δ4,16-pregnadiene-3,20-dione, Δ4,15-pregnadiene-17α-ol-3,20-dione, 16-methyl-Δ5,16-pregnadiene-3β-ol-20-one, and Δ5,15-pregnadiene-3β,17α-diol-20-one were isolated. The formation of the latter is due to alkali-catalyzed opening of the epoxide ring in the presence of the strong base, that methyllithium is.

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Authors and Affiliations

  1. Ordzhonikidze All-Union Chemical and Pharmaceutical Scientific-Research Institute, USSR

    L. V. Sokolova, L. I. Klimova, Z. A. Yaroslavtseva, E. M. Kaminka & N. N. Suvorov

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  1. L. V. Sokolova
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  2. L. I. Klimova
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  3. Z. A. Yaroslavtseva
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  4. E. M. Kaminka
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  5. N. N. Suvorov
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Khimiya Prirodnykh Soedinenii, Vol. 6, No. 1, pp. 33–38, 1970

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Sokolova, L.V., Klimova, L.I., Yaroslavtseva, Z.A. et al. Steroids. Chem Nat Compd 6, 30–34 (1970). https://doi.org/10.1007/BF00564153

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  • DOI: https://doi.org/10.1007/BF00564153

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