Synthesis of pregnenoic acid derivatives possessing structural elements of prostaglandins.
Pregneoic acid derivative V in which the character of functional groups and distances between them (expressed in terms of C-C bonds) resemble those occurring in prostaglandins has been synthetised. 3beta-Hydroxyandrost-5-en-17-one acetate VII was converted to ethyl 3beta-acetoxypregn-5-en-21-oate XIIa via a Reformatsky reaction followed by dehydration of adduct VIIIa and selective hydrogenation of the diene X. Compound XIIa was then transformed into trienone XIII by oxidation of the 3beta-hydroxy-5-ene XIIc with DDQ. The trienone XIII was subsequently epoxidised with alkaline hydrogen peroxide and m-chloroperbenzoic acid to give diepoxide XV which was reduced with aluminum amalgam to the final product V.
D000818:Animals; D002417:Cattle; D008297:Male; D008722:Methods; D008861:Microsomes / Q000187:drug effects / Q000378:metabolism; D011283:Pregnenes / Q000138:chemical synthesis / Q000494:pharmacology; D011453:Prostaglandins / Q000096:biosynthesis; D012669:Seminal Vesicles / Q000187:drug effects / Q000378:metabolism; D013329:Structure-Activity Relationship
D011283:Pregnenes; D011453:Prostaglandins; C016076:methyl-1alpha, 7alpha-dihydroxy-3-oxopregn-4-en-21-oate