title: A concise synthesis of ent-Cholesterol.
abstract: ent-Cholesterol was synthesized in 16 steps from commercially available (S)-citronellol. The overall yield for the synthesis was 2.0%. This route is amenable to gram-scale preparation of ent-cholesterol. Isotopic incorporation near the end of the synthesis was achieved using labeled methyl iodide. This synthesis is the most practical to date and will make ent-cholesterol more readily available to use as a probe of the function and metabolism of cholesterol.
authors.affiliation: Department of Chemistry, 1102 Natural Sciences II, University of California, Irvine, Irvine, CA 92697, USA.
authors.forename: Jitendra D
authors.initials: JD
authors.lastname: Belani
authors.forename: Scott D
authors.initials: SD
authors.lastname: Rychnovsky
mesh_terms: D000080462:Acyclic Monoterpenes; D002784:Cholesterol / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D039821:Monoterpenes / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000080462:Acyclic Monoterpenes; D039821:Monoterpenes; D002784:Cholesterol; C007078:citronellol