title: Solid-phase selenium-catalyzed selective allylic chlorination of polyprenoids: facile syntheses of biologically active terpenoids.
abstract: Regioselective halogenation of the terminal isopropylidene unit of different acyclic polyolefinic polyprenoids (farnesyl acetate, geranylgeranyl acetate, squalene, etc.) using NCS/catalytic polymer-supported selenenyl bromide is described; good to excellent yields are obtained (68-96%). The first applications of this protocol include the concise synthesis of bioactive terpenoids 1-3.
authors.affiliation: Department of Organic Chemistry, Institute of Biotechnology, University of Granada, Avda. Fuentenueva, 18071, Granada, Spain. afbarre@goliat.ugr.es
authors.forename: Alejandro F
authors.initials: AF
authors.lastname: Barrero
authors.forename: José F
authors.initials: JF
authors.lastname: Quílez Del Moral
authors.forename: M Mar
authors.initials: MM
authors.lastname: Herrador
authors.forename: Manuel
authors.initials: M
authors.lastname: Cortés
authors.forename: Pilar
authors.initials: P
authors.lastname: Arteaga
authors.forename: Julieta V
authors.initials: JV
authors.lastname: Catalan
authors.forename: Elena M
authors.initials: EM
authors.lastname: Sanchez
authors.forename: Jesús F
authors.initials: JF
authors.lastname: Arteaga
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D000498:Allyl Compounds / Q000737:chemistry*; D002384:Catalysis; D006843:Hydrocarbons, Chlorinated / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D012643:Selenium / Q000737:chemistry*; D013185:Squalene / Q000737:chemistry; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000475:Alkenes; D000498:Allyl Compounds; D006843:Hydrocarbons, Chlorinated; D013729:Terpenes; D013185:Squalene; D012643:Selenium