title: Synthesis of side-chain oxysterols and their enantiomers through cross-metathesis reactions of Δ22steroids.
abstract: A synthetic route that utilizes a cross-metathesis reaction with Δ22steroids has been developed to prepare sterols with varying C-27 side-chains. Natural sterols containing hydroxyl groups at the 25 and (25R)-26 positions were prepared. Enantiomers of cholesterol and (3β,25R)-26-hydroxycholesterol (27-hydroxycholesterol) trideuterated at C-19 were prepared for future biological studies.
authors.affiliation: Department of Chemistry, Carthage College, 2001 Alford Park, Kenosha, WI 53140, USA. Electronic address: dbrownholland@centenary.edu.
authors.forename: David P
authors.initials: DP
authors.lastname: Brownholland
authors.affiliation: Department of Developmental Biology, Washington University in St. Louis, 660 South Euclid Avenue, St. Louis, MO 63110, USA; Department of Anesthesiology, Washington University in St. Louis, 660 South Euclid Avenue, St. Louis, MO 63110, USA; Department of Psychiatry, Washington University in St. Louis, 660 South Euclid Avenue, St. Louis, MO 63110, USA. Electronic address: dcovey@wustl.edu.
authors.forename: Douglas F
authors.initials: DF
authors.lastname: Covey
mesh_terms: D002384:Catalysis; D015394:Molecular Structure; D000072376:Oxysterols / Q000737:chemistry*; D012428:Ruthenium / Q000737:chemistry; D013237:Stereoisomerism; D013256:Steroids / Q000737:chemistry*
chemical_list: D000072376:Oxysterols; D013256:Steroids; D012428:Ruthenium
keywords: Cross-metathesis; Grubbs catalyst; Ruthenium catalyst; Side-chain oxysterols; ent-steroids; Δ(22)-steroids