Total Synthesis of the Resveratrol Oligomers (±)‐Ampelopsin B and (±)‐ϵ‐Viniferin

The total synthesis of the resveratrol dimers (±)‐ampelopsin B and (±)‐ϵ‐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 adv...

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Autores principales: Lindgren, Anders E. G., Öberg, Christopher T., Hillgren, J. Mikael, Elofsson, Mikael
Formato: Online Artículo Texto
Lenguaje:English
Publicado: WILEY‐VCH Verlag 2015
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4737285/
http://dx.doi.org/10.1002/ejoc.201501486
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author Lindgren, Anders E. G.
Öberg, Christopher T.
Hillgren, J. Mikael
Elofsson, Mikael
author_facet Lindgren, Anders E. G.
Öberg, Christopher T.
Hillgren, J. Mikael
Elofsson, Mikael
author_sort Lindgren, Anders E. G.
collection PubMed
description The total synthesis of the resveratrol dimers (±)‐ampelopsin B and (±)‐ϵ‐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.
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spelling pubmed-47372852016-02-12 Total Synthesis of the Resveratrol Oligomers (±)‐Ampelopsin B and (±)‐ϵ‐Viniferin Lindgren, Anders E. G. Öberg, Christopher T. Hillgren, J. Mikael Elofsson, Mikael European J Org Chem Communications The total synthesis of the resveratrol dimers (±)‐ampelopsin B and (±)‐ϵ‐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. WILEY‐VCH Verlag 2015-12-11 2016-01 /pmc/articles/PMC4737285/ http://dx.doi.org/10.1002/ejoc.201501486 Text en © 2016 The Authors. Published by WILEY‐VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution Non‐Commercial NoDerivs License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made. Open access.
spellingShingle Communications
Lindgren, Anders E. G.
Öberg, Christopher T.
Hillgren, J. Mikael
Elofsson, Mikael
Total Synthesis of the Resveratrol Oligomers (±)‐Ampelopsin B and (±)‐ϵ‐Viniferin
title Total Synthesis of the Resveratrol Oligomers (±)‐Ampelopsin B and (±)‐ϵ‐Viniferin
title_full Total Synthesis of the Resveratrol Oligomers (±)‐Ampelopsin B and (±)‐ϵ‐Viniferin
title_fullStr Total Synthesis of the Resveratrol Oligomers (±)‐Ampelopsin B and (±)‐ϵ‐Viniferin
title_full_unstemmed Total Synthesis of the Resveratrol Oligomers (±)‐Ampelopsin B and (±)‐ϵ‐Viniferin
title_short Total Synthesis of the Resveratrol Oligomers (±)‐Ampelopsin B and (±)‐ϵ‐Viniferin
title_sort total synthesis of the resveratrol oligomers (±)‐ampelopsin b and (±)‐ϵ‐viniferin
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4737285/
http://dx.doi.org/10.1002/ejoc.201501486
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AT elofssonmikael totalsynthesisoftheresveratrololigomersampelopsinbandeviniferin

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