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 condi...
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| Veröffentlicht in: | Organic & biomolecular chemistry 2008-01, Vol.6 (14), p.2619-2627 |
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| container_issue | 14 |
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| container_title | Organic & biomolecular chemistry |
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| creator | Raffaelli, Barbara Pohjoispää, Monika Hase, Tapio Cardin, Christine J Gan, Yu Wähälä, Kristiina |
| description | 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. |
| doi_str_mv | 10.1039/b801593g |
| format | Article |
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| fulltext | fulltext |
| identifier | ISSN: 1477-0520 |
| ispartof | Organic & biomolecular chemistry, 2008-01, Vol.6 (14), p.2619-2627 |
| issn | 1477-0520 1477-0539 |
| language | eng |
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| source | MEDLINE; Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Ethanol - chemistry Furans - chemistry Lactones - chemistry Lignans - chemistry Mass Spectrometry Oxygen Isotopes Protons Sodium Hydroxide - chemistry Stereoisomerism Water - chemistry |
| title | Stereochemistry and rearrangement reactions of hydroxylignanolactones |
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