Stereochemistry and rearrangement reactions of hydroxylignanolactones.
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.
Raffaelli
Barbara
B
Department of Chemistry, Laboratory of Organic Chemistry, University of Helsinki, P.O. Box 55, FIN-00014, Finland.
Pohjoispää
Monika
M
Hase
Tapio
T
Cardin
Christine J
CJ
Gan
Yu
Y
Wähälä
Kristiina
K
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
D005663:Furans; D007783:Lactones; D017705:Lignans; D010103:Oxygen Isotopes; D011522:Protons; D014867:Water; D000431:Ethanol; D012972:Sodium Hydroxide; C068935:matairesinol