Steroidal seven-membered A-ring epoxy lactones by oxidation of the corresponding Delta 4-3-ketosteroids.
Treatment of Delta 4-3-ketosteroids with m-chloroperbenzoic acid at 0 degrees C produced the corresponding steroidal seven-membered A-ring epoxy lactones. The adopted procedure allowed for efficient recovery and separation of the products with definite stereochemistry.
Gioia
Maria L Di
ML
Dipartimento di Scienze Farmaceutiche, Università degli Studi della Calabria, Via Ponte P. Bucci, Cubo 15/C, I-87036 Arcavacata di Rende (CS), Italy.
Leggio
Antonella
A
Pera
Adolfo Le
AL
Perri
Francesca
F
Pitrelli
Andrea F
AF
Liguori
Angelo
A
D002723:Chlorobenzoates / Q000737:chemistry; D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D007664:Ketosteroids / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D013256:Steroids / Q000737:chemistry*
D002723:Chlorobenzoates; D004852:Epoxy Compounds; D007664:Ketosteroids; D007783:Lactones; D013256:Steroids; C000433:3-chloroperbenzoic acid