Structure elucidation of new compounds from acidic treatment of the progestins gestodene and drospirenone.
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.
Colombo
Diego
D
Dipartimento di Chimica, Biochimica e Biotecnologie per la Medicina, Università di Milano, Italy. diego.colombo@unimi.it
Bombieri
Gabriella
G
Lenna
Roberto
R
Marchini
Nicoletta
N
Modica
Emilia
E
Scala
Antonio
A
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*
D000736:Androstenes; D009652:Norpregnenes; D045167:Progesterone Congeners; C033273:Gestodene; C035144:drospirenone