One-pot efficient synthesis of 13(R),14(R)-epoxy-17β-methyl-20(S)-hydroxyl-18-nor-pregna-4-en-3-one via a tandem epoxidation-rearrangement-epoxidation reaction sequence

• A one-pot synthesis method for an 18-norsteroids has been developed.
• Controlled experiments have proven the proposed mechanism of tandem epoxidation-rearrangement-epoxidation reaction sequence.
• This method is suitable for Δ17 (20), Δ13 (14), as well as 17ζ, 20ζ-epoxy steroid skeletons.
• This method has the merit of retention of the Δ4, 3-keto group because of the chemo-selectivity.
• XRD of 13(R),14(R)-epoxy-17β-methyl-20(S)-hydroxyl-18-nor-pregna-4-en-3-one shows the epoxide adopts a cis configuration.

One-pot synthesis of an 18-norsteroid compound, 13(R),14(R)-epoxy-17β-methyl-20(S)-hydroxyl-18-nor-pregna-4-en-3-one has been achieved with peracetic acid/acetic acid under a mild condition, via a proved tandem epoxidation-rearrangement-epoxidation sequence. Its structure was designated on the basis of NMR and X-ray crystallography data.

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