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Reaction of 5β,6β-epoxy-16α,17α-cyclohexapregnane with methylmagnesium iodide

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Abstract

On treatment with methylmagnesium iodide, 3β-acetoxy-5β,6β-epoxy-16α,17α-cyclo-hexapregnan-20-one undergoes 3-O-deacetylation along with the opening of the 5β,6β-epoxide ring to form 5α-methyl-6β-hydroxy steroid and the 6α-methyl-6β-hydroxy isomer, the 20-keto group remaining intact.

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Correspondence to I. S. Levina.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 2037–2040, September, 2013.

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Levina, I.S., Kulikova, L.E., Kachala, V.V. et al. Reaction of 5β,6β-epoxy-16α,17α-cyclohexapregnane with methylmagnesium iodide. Russ Chem Bull 62, 2037–2040 (2013). https://doi.org/10.1007/s11172-013-0295-7

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  • DOI: https://doi.org/10.1007/s11172-013-0295-7

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