Stereochemistry and rearrangement reactions of hydroxylignanolactones |
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| Authors: | Raffaelli Barbara Pohjoispää Monika Hase Tapio Cardin Christine J Gan Yu Wähälä Kristiina |
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| Institution: | Department of Chemistry, Laboratory of Organic Chemistry, University of Helsinki, P.O. Box 55, FIN-00014, Finland. |
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| 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. |
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