Stereochemistry and rearrangement reactions of hydroxylignanolactones

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
Hauptverfasser: Raffaelli, Barbara, Pohjoispää, Monika, Hase, Tapio, Cardin, Christine J, Gan, Yu, Wähälä, Kristiina
Format: Artikel
Sprache:eng
Schlagworte:
Ethanol - chemistry
Furans - chemistry
Lactones - chemistry
Lignans - chemistry
Mass Spectrometry
Oxygen Isotopes
Protons
Sodium Hydroxide - chemistry
Stereoisomerism
Water - chemistry
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Zusammenfassung: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.
ISSN:1477-0520
1477-0539
DOI:10.1039/b801593g