Cyclopropylmethyl Protection of Phenols: Total Synthesis of the Resveratrol Dimers Anigopreissin A and Resveratrol–Piceatannol Hybrid

We demonstrate the versatile use of the cyclopropylmethyl group to protect phenols through the total synthesis of two benzofuran‐based natural products, that is, anigopreissin A and the resveratrol–piceatannol hybrid. This protecting group is a good alternative to the conventional methyl group, owin...

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Detalles Bibliográficos
Autores principales: Kumar, Arvind, Saleeb, Michael, Werz, Dominik, Elofsson, Mikael
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2018
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6276102/
https://www.ncbi.nlm.nih.gov/pubmed/30524921
http://dx.doi.org/10.1002/open.201800214
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author Kumar, Arvind
Saleeb, Michael
Werz, Dominik
Elofsson, Mikael
author_facet Kumar, Arvind
Saleeb, Michael
Werz, Dominik
Elofsson, Mikael
author_sort Kumar, Arvind
collection PubMed
description We demonstrate the versatile use of the cyclopropylmethyl group to protect phenols through the total synthesis of two benzofuran‐based natural products, that is, anigopreissin A and the resveratrol–piceatannol hybrid. This protecting group is a good alternative to the conventional methyl group, owing to the feasibility of introduction, stability under a variety of conditions, and its relative ease of removal under different acidic conditions.
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spelling pubmed-62761022018-12-06 Cyclopropylmethyl Protection of Phenols: Total Synthesis of the Resveratrol Dimers Anigopreissin A and Resveratrol–Piceatannol Hybrid Kumar, Arvind Saleeb, Michael Werz, Dominik Elofsson, Mikael ChemistryOpen Communications We demonstrate the versatile use of the cyclopropylmethyl group to protect phenols through the total synthesis of two benzofuran‐based natural products, that is, anigopreissin A and the resveratrol–piceatannol hybrid. This protecting group is a good alternative to the conventional methyl group, owing to the feasibility of introduction, stability under a variety of conditions, and its relative ease of removal under different acidic conditions. John Wiley and Sons Inc. 2018-11-05 /pmc/articles/PMC6276102/ /pubmed/30524921 http://dx.doi.org/10.1002/open.201800214 Text en © 2018 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes.
spellingShingle Communications
Kumar, Arvind
Saleeb, Michael
Werz, Dominik
Elofsson, Mikael
Cyclopropylmethyl Protection of Phenols: Total Synthesis of the Resveratrol Dimers Anigopreissin A and Resveratrol–Piceatannol Hybrid
title Cyclopropylmethyl Protection of Phenols: Total Synthesis of the Resveratrol Dimers Anigopreissin A and Resveratrol–Piceatannol Hybrid
title_full Cyclopropylmethyl Protection of Phenols: Total Synthesis of the Resveratrol Dimers Anigopreissin A and Resveratrol–Piceatannol Hybrid
title_fullStr Cyclopropylmethyl Protection of Phenols: Total Synthesis of the Resveratrol Dimers Anigopreissin A and Resveratrol–Piceatannol Hybrid
title_full_unstemmed Cyclopropylmethyl Protection of Phenols: Total Synthesis of the Resveratrol Dimers Anigopreissin A and Resveratrol–Piceatannol Hybrid
title_short Cyclopropylmethyl Protection of Phenols: Total Synthesis of the Resveratrol Dimers Anigopreissin A and Resveratrol–Piceatannol Hybrid
title_sort cyclopropylmethyl protection of phenols: total synthesis of the resveratrol dimers anigopreissin a and resveratrol–piceatannol hybrid
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6276102/
https://www.ncbi.nlm.nih.gov/pubmed/30524921
http://dx.doi.org/10.1002/open.201800214
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