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Total Synthesis of the Resveratrol Oligomers (+/-)-Ampelopsin B and (+/-)-E-Viniferin
Umeå University, Faculty of Science and Technology, Department of Chemistry.
Umeå University, Faculty of Science and Technology, Department of Chemistry.
Umeå University, Faculty of Science and Technology, Department of Chemistry.
Umeå University, Faculty of Science and Technology, Department of Chemistry.
2016 (English)In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 3, 426-429 p.Article in journal (Refereed) Published
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Abstract [en]

The total synthesis of the resveratrol dimers (+/-)-ampelopsin B and (+/-)-E-viniferin is reported. Highlights of the approach include the use of cyclopropylmethyl groups to protect aromatic alcohols. This group allows an acid promoted three-step, one-pot deprotection-epimerization-cyclization of an advanced intermediate to give (+/-)-ampelopsin B. An important advantage with our strategy is the possibility of synthesizing analogs to these natural products to further study the chemistry and biology of resveratrol oligomers.

Place, publisher, year, edition, pages
2016. no 3, 426-429 p.
Keyword [en]
Protecting groups, Cyclopropylmethyl, Polyphenols, Total synthesis, Natural products
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:umu:diva-116747DOI: 10.1002/ejoc.201501486ISI: 000368815700002OAI: oai:DiVA.org:umu-116747DiVA: diva2:904798
Available from: 2016-02-19 Created: 2016-02-11 Last updated: 2017-11-30Bibliographically approved

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Lindgren, Anders E. G.Oberg, Christopher T.Hillgren, J. MikaelElofsson, Mikael
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