title: Stereospecificity in the Au-catalysed cyclisation of monoallylic diols. Synthesis of (+)-isoaltholactone.
abstract: We describe a concise synthesis of (+)-isoaltholactone via a Au-catalysed cyclisation of a monoallylic diol to form the tetrahydrofuranyl ring. Analogous cyclisations show that the stereochemical outcome is dictated by the stereochemistry of the diol substrate.
authors.affiliation: Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK.
authors.forename: William P
authors.initials: WP
authors.lastname: Unsworth
authors.forename: Kiri
authors.initials: K
authors.lastname: Stevens
authors.forename: Scott G
authors.initials: SG
authors.lastname: Lamont
authors.forename: Jeremy
authors.initials: J
authors.lastname: Robertson
mesh_terms: D002384:Catalysis; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D006046:Gold / Q000737:chemistry*; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D005663:Furans; D011753:Pyrones; C459359:altholactone; D006046:Gold