Studies directed toward synthesis of quassinoids VII. Conversion of chenodeoxycholic acid to a delta-lactone quassinoid analog and generation of A-ring diosphenol acetate derivatives of deoxycholic acid.
Chenodeoxycholic acid was converted to a new 5,14-epi-28,30-dinorquassinoid analog. Two isomeric A-ring diosphenol acetate derivatives of deoxycholic acid were synthesized. A 3-oxo-5 beta-steroid was transformed to a 4-acetoxy-3-oxo-delta 4-steroid by treatment with base and oxygen or to a 2-acetoxy-3-oxo-delta 2-steroid by reaction with cupric chloride in refluxing acetic acid followed by acetylation. Ketene extrusion is a characteristic mass spectral fragmentation of these diosphenol acetates.
D055598:Chemical Phenomena; D002621:Chemistry; D002635:Chenodeoxycholic Acid / Q000031:analogs & derivatives*; D003840:Deoxycholic Acid / Q000031:analogs & derivatives*; D007783:Lactones / Q000138:chemical synthesis*; D008722:Methods; D010616:Phenanthrenes / Q000138:chemical synthesis*
D007783:Lactones; D010616:Phenanthrenes; D003840:Deoxycholic Acid; D002635:Chenodeoxycholic Acid; C025005:methyl 3 alpha-acetoxy-13 alpha-carbomethoxy-16-oxo-17-oxa-13,17-seco-7 alpha,17-cyclo-5 beta-androstane