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Transformations of lignans. Part 10: Acid-catalysed rearrangements of arboreol and wodeshiol and conversion of gmelanone oxime into a dihydropyranone derivative |
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| Authors: | Revuru Venkateswarlu Chakicherla Kamakshi Syed GA Moinuddin Mangala P Gowri Robert S Ward Andrew Pelter Simon J Coles |
| Institution: | a Department of Organic Chemistry, Andhra University, Visakhapatnam-530003, AP, India b Department of Chemistry, University of Wales Swansea, Singleton Park, Swansea SA2 8PP, UK c EPSRC National Crystallography Service, School of Chemistry, University of Southampton, Southampton SO17 1BJ, UK |
| Abstract: | The synthesis of gmelanone 2 by a pinacol-type rearrangement of arboreol 1 supports its biogenesis and confirms its relative and absolute configuration. The further transformation of gmelanone oxime 12 into the dihydropyranone oxime 13 supports the intermediacy of gmelanone like intermediates in the rearrangements of furofuran lignans to pyran derivatives. In contrast, acid-catalysed rearrangement of wodeshiol 7 affords the dihydropyranone 8. |
| Keywords: | Lignans Pinacol rearrangement Biomimetic synthesis Oxime rearrangement |
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