title: 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.
abstract: 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.
authors.affiliation: School of Chemical Engineering and Energy, Zhengzhou University, Zhengzhou 450001, China; College of Chemical Engineering and Pharmaceutical, Henan University of Science and Technology, Luoyang 471023, China.
authors.forename: Shu-Xiao
authors.initials: SX
authors.lastname: Feng
authors.forename: Ya-Dong
authors.initials: YD
authors.lastname: Zhang
mesh_terms: D004092:20-alpha-Dihydroprogesterone / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D019342:Acetic Acid / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis*; D002384:Catalysis; D018360:Crystallography, X-Ray; D004852:Epoxy Compounds / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009653:Norprogesterones / Q000138:chemical synthesis*; D010463:Peracetic Acid / Q000737:chemistry
chemical_list: D001688:Biological Products; D004852:Epoxy Compounds; D009653:Norprogesterones; D004092:20-alpha-Dihydroprogesterone; D010463:Peracetic Acid; D019342:Acetic Acid
keywords: Epoxidation-rearrangement-epoxidation; One-pot; Peracetic acid/acetic acid; Tandem reaction