title: Stereochemistry and rearrangement reactions of hydroxylignanolactones.
abstract: Various conflicting data on the rearrangement and absolute stereochemistry of hydroxylignano-9,7'-lactones are resolved using 18O labeled compounds, also confirmed by an X-ray analysis of a pure lignano-9,7'-lactone enantiomer, obtained for the first time. Under NaH/DMF rearrangement conditions a silyl protected hydroxylignano-9,9'-lactone underwent an unexpected silyl migration.
authors.affiliation: Department of Chemistry, Laboratory of Organic Chemistry, University of Helsinki, P.O. Box 55, FIN-00014, Finland.
authors.forename: Barbara
authors.initials: B
authors.lastname: Raffaelli
authors.forename: Monika
authors.initials: M
authors.lastname: Pohjoispää
authors.forename: Tapio
authors.initials: T
authors.lastname: Hase
authors.forename: Christine J
authors.initials: CJ
authors.lastname: Cardin
authors.forename: Yu
authors.initials: Y
authors.lastname: Gan
authors.forename: Kristiina
authors.initials: K
authors.lastname: Wähälä
mesh_terms: D000431:Ethanol / Q000737:chemistry; D005663:Furans / Q000737:chemistry; D007783:Lactones / Q000737:chemistry*; D017705:Lignans / Q000737:chemistry; D013058:Mass Spectrometry; D010103:Oxygen Isotopes; D011522:Protons; D012972:Sodium Hydroxide / Q000737:chemistry; D013237:Stereoisomerism; D014867:Water / Q000737:chemistry
chemical_list: D005663:Furans; D007783:Lactones; D017705:Lignans; D010103:Oxygen Isotopes; D011522:Protons; D014867:Water; D000431:Ethanol; D012972:Sodium Hydroxide; C068935:matairesinol