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Total Synthesis of Viniferifuran, Resveratrol-Piceatannol Hybrid, Anigopreissin A and Analogues: Investigation of Demethylation Strategies
Umeå University, Faculty of Science and Technology, Department of Chemistry.
Umeå University, Faculty of Science and Technology, Department of Chemistry.
2016 (English)In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 358, no 24, 4085-4092 p.Article in journal (Refereed) Published
Abstract [en]

Resveratrol-based natural products constitute a valuable source of unique compounds with diverse biological activities. In this report we investigate demethylation strategies to minimize formation of cyclized and dimerized products during the synthesis of viniferifuran and analogues. We found that boron trichloride/tetra-n-butylammonium iodide (BCl3/TBAI) is typically more effective than boron tribromide (BBr3). Based on these findings we carried out the first syntheses of dehydro-δ-viniferin, resveratrol-piceatannol hybrid and anigopreissin A. In addition, we have developed a short and efficient route to viniferifuran that was obtained in 13% yield over six steps.

Place, publisher, year, edition, pages
Wiley-VCH Verlagsgesellschaft, 2016. Vol. 358, no 24, 4085-4092 p.
Keyword [en]
demethylation, natural products, polyphenols, resveratrol oligomers, stilbenoids, total synthesis
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:umu:diva-129956DOI: 10.1002/adsc.201601089ISI: 000391810000022OAI: oai:DiVA.org:umu-129956DiVA: diva2:1063522
Available from: 2017-01-10 Created: 2017-01-10 Last updated: 2017-08-15Bibliographically approved

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CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • harvard1
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf