Conclusions
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1.
Acetolysis in the presence of carbethoxyhydrazine in acetic acid was studied on the example of some 21-methoxymethyl-16α,17α-epoxysteroids [(Ia, b), (V)]. Removal of the carbonyl protection gives the corresponding 16α,17α-dihydroxy derivatives, the products of the cis-opening of the oxide ring, which were obtained by counter synthesis from Δ16-20-keto-21-methoxymethylsteroids.
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2.
Instead of the usual trans-opening of the oxide ring, the acetolysis of epoxyketones (Ib) and (V) in the presence of sulfuric acid leads to the formation of steroid compounds (VII) and (VIII), with additional heterocycles E that contain a side chain.
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See [1] for communication 72.
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 2, pp. 411–414, February, 1975.
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Kamernitskii, A.V., Ol'gina, N.M., Reshetova, I.G. et al. Transformed steroids. Russ Chem Bull 24, 339–342 (1975). https://doi.org/10.1007/BF00925782
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DOI: https://doi.org/10.1007/BF00925782