title: A facile synthesis of lanost-8-en-3 beta-ol-24-one (24-ketolanosterol). An inhibitor of 3-hydroxy-3-methylglutaryl coenzyme A reductase.
abstract: A facile chemical synthesis of lanost-8-en-3 beta-ol-24-one (24-ketolanosterol) is described. This compound was found to be a potent inhibitor of 3-hydroxy-3-methylglutaryl (HMG) CoA reductase activity in cultured mouse L cells. The synthetic scheme developed in this study utilizes commercial lanosterol as a starting material and involves selective hydroboration of the C-24 double bond followed by oxidation of the carbon-boron bond at C-24 by pyridinium chlorochromate (PCC).
authors.affiliation: Department of Chemistry, Auburn University, AL 36849.
authors.forename: E J
authors.initials: EJ
authors.lastname: Parish
authors.forename: H
authors.initials: H
authors.lastname: Honda
authors.forename: S
authors.initials: S
authors.lastname: Chitrakorn
authors.forename: F R
authors.initials: FR
authors.lastname: Taylor
mesh_terms: D000818:Animals; D002478:Cells, Cultured; D019161:Hydroxymethylglutaryl-CoA Reductase Inhibitors; D007739:L Cells; D007810:Lanosterol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D051379:Mice
chemical_list: D019161:Hydroxymethylglutaryl-CoA Reductase Inhibitors; D007810:Lanosterol; C059133:lanosteryl acetate; C059132:lanost-8-en-3-ol-24-one