Synthesis of 15-keto-6beta, 7beta-methyleneprogesterone. Effect of the 6beta, 7beta-methylene group on mineralocorticoid activity.
15-Ketoprogesterone is as active as spironolactone in blocking the mineralocorticoid effect of deoxycorticosterone acetate. This activity is reduced when a methylene group is attached to the 6beta, 7beta position. The title compound was prepared from 15alpha-acetoxy-6-dehydroprogesterone. Methylenation of the delta6 double bond with dimethyloxosulfonium methylide proceeds steroselectively from the beta side of the molecule.
D000818:Animals; D001952:Bridged-Ring Compounds / Q000138:chemical synthesis / Q000494:pharmacology; D003900:Desoxycorticosterone / Q000037:antagonists & inhibitors*; D007664:Ketosteroids / Q000138:chemical synthesis / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D009904:Optical Rotation; D011374:Progesterone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D001952:Bridged-Ring Compounds; D007664:Ketosteroids; D003900:Desoxycorticosterone; D011374:Progesterone