title: A highly enantioselective total synthesis of (+)-goniodiol.
abstract: A high-yielding enantioselective total synthesis of the bioactive styryllactone (+)-goniodiol has been realised, starting from readily available (S)-glycidol. A key step is an oxygen-to-carbon rearrangement of a silyl enol ether linked via an anomeric centre, facilitating the rapid and diastereoselective construction of this functionalised system.
authors.affiliation: Biological and Biophysical Chemistry Section, Department of Chemistry, Imperial College London, UK. e.tate@imperial.ac.uk
authors.forename: Edward W
authors.initials: EW
authors.lastname: Tate
authors.forename: Darren J
authors.initials: DJ
authors.lastname: Dixon
authors.forename: Steven V
authors.initials: SV
authors.lastname: Ley
mesh_terms: D004852:Epoxy Compounds / Q000737:chemistry; D004986:Ether; D007783:Lactones / Q000138:chemical synthesis; D020005:Propanols / Q000737:chemistry; D011753:Pyrones / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D004852:Epoxy Compounds; D007783:Lactones; D020005:Propanols; D011753:Pyrones; C446739:goniodiol; D004986:Ether; C004312:glycidol