title: Stereoselection in the prins-pinacol synthesis of 2,2-disubstituted 4-acyltetrahydrofurans. Enantioselective synthesis of (-)-citreoviral.
abstract: [reaction: see text] The condensation of allylic diols with unsymmetrical ketones proceeds with high stereoselection to form 2,2-disubstituted 4-acyltetrahydrofurans when the alpha-substituents of the ketone differ substantially in size. A Prins-pinacol condensation of this type is the central strategic step in an enantioselective synthesis of (-)-citreoviral.
authors.affiliation: Department of Chemistry, University of California, Irvine 92697-2025, USA.
authors.forename: N
authors.initials: N
authors.lastname: Hanaki
authors.forename: J T
authors.initials: JT
authors.lastname: Link
authors.forename: D W
authors.initials: DW
authors.lastname: MacMillan
authors.forename: L E
authors.initials: LE
authors.lastname: Overman
authors.forename: W G
authors.initials: WG
authors.lastname: Trankle
authors.forename: J A
authors.initials: JA
authors.lastname: Wurster
mesh_terms: D001313:Aurovertins / Q000138:chemical synthesis*; D005663:Furans / Q000138:chemical synthesis*; D009183:Mycotoxins / Q000138:chemical synthesis; D009498:Neurotoxins / Q000138:chemical synthesis; D013237:Stereoisomerism
chemical_list: D001313:Aurovertins; D005663:Furans; D009183:Mycotoxins; D009498:Neurotoxins; C014416:citreoviridin