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Steroids

XXXVII. The stereospecificity of the hydrogenation of 16α-methyl-3-oxo-Δ4-unsaturated compounds

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Chemistry of Natural Compounds Aims and scope

Conclusions

1. It has been established that the hydrogenation of 11α-hydroxy-16α-methylpregn-4-ene-3,20-dione and of 16α-methylpregn-4-ene-3, 11 20-trione over 10% palladium on calcium carbonate in pyridine takes place stereospecifically and is determined by the substituent at C11.

2. It has been shown that a 16α-methyl group has practically no influence on the stereochemical directivity of the hydrogenation of the ethylenic bond of the Δ4-3-oxo system.

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Khimiya Prirodnykh Soedinenii, Vol. 6, No. 1, pp. 53–56, 1970

For part XXXVI se KhPS [Chemistry of Natural Compounds], 6, 33, 1970 [in this issue].

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Shner, V.F., Sadovskaya, V.L. & Suvorov, N.N. Steroids. Chem Nat Compd 6, 48–51 (1970). https://doi.org/10.1007/BF00564156

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  • DOI: https://doi.org/10.1007/BF00564156

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