title: Structure elucidation of new compounds from acidic treatment of the progestins gestodene and drospirenone.
abstract: Gestodene acidic treatment afforded a single rearrangement product, namely 13-beta-ethyl-18,19-dinorpregna-4,14,16-trien-3,20-dione 3, which was originated through HCl-catalyzed Rupe rearrangement. Drospirenone acidic treatment yielded two epimeric lactones by addition of HCl to the 6beta,7beta-cyclopropane ring, namely 7beta-(chloromethyl)-15beta,16beta-methylene-3-oxo-17beta-pregn-4-ene-21,17-carbolactone 4 and 7beta-(chloromethyl)-15beta,16beta-methylene-3-oxo-17alpha-pregn-4-ene-21,17-carbolactone 5. The structure of the compounds was assessed by spectroscopic and crystallographic methods.
authors.affiliation: Dipartimento di Chimica, Biochimica e Biotecnologie per la Medicina, Università di Milano, Italy. diego.colombo@unimi.it
authors.forename: Diego
authors.initials: D
authors.lastname: Colombo
authors.forename: Gabriella
authors.initials: G
authors.lastname: Bombieri
authors.forename: Roberto
authors.initials: R
authors.lastname: Lenna
authors.forename: Nicoletta
authors.initials: N
authors.lastname: Marchini
authors.forename: Emilia
authors.initials: E
authors.lastname: Modica
authors.forename: Antonio
authors.initials: A
authors.lastname: Scala
mesh_terms: D000736:Androstenes / Q000737:chemistry*; D018360:Crystallography, X-Ray; D008954:Models, Biological; D008958:Models, Molecular; D015394:Molecular Structure; D009652:Norpregnenes / Q000737:chemistry*; D045167:Progesterone Congeners / Q000138:chemical synthesis*
chemical_list: D000736:Androstenes; D009652:Norpregnenes; D045167:Progesterone Congeners; C033273:Gestodene; C035144:drospirenone