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Desymmetrization of C (2)‐Symmetric Bis(Boronic Esters) by Zweifel Olefinations

anti‐Configured 1,3‐dimethyl deoxypropionate motifs are important sub structures in natural products. Herein, we describe a bidirectional approach for the rapid construction of natural products featuring such motifs by using C (2)‐symmetrical 1,3‐bis(boronic esters). As for its application in conver...

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Autores principales: Linne, Yannick, Schönwald, Axel, Weißbach, Sebastian, Kalesse, Markus
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7384159/
https://www.ncbi.nlm.nih.gov/pubmed/32068298
http://dx.doi.org/10.1002/chem.202000599
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author Linne, Yannick
Schönwald, Axel
Weißbach, Sebastian
Kalesse, Markus
author_facet Linne, Yannick
Schönwald, Axel
Weißbach, Sebastian
Kalesse, Markus
author_sort Linne, Yannick
collection PubMed
description anti‐Configured 1,3‐dimethyl deoxypropionate motifs are important sub structures in natural products. Herein, we describe a bidirectional approach for the rapid construction of natural products featuring such motifs by using C (2)‐symmetrical 1,3‐bis(boronic esters). As for its application in convergent syntheses it was important to establish a selective mono‐Zweifel olefination we describe the scope and limitations by using different 1,3‐bis(boronic esters) and nucleophiles. This protocol takes advantage of the combination of the Hoppe–Matteson–Zweifel chemistry, which was elegantly put into practice by Aggarwal et al. In order to show its applicability the total syntheses of two natural products, serricornin and (+)‐invictolide, were performed.
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spelling pubmed-73841592020-07-28 Desymmetrization of C (2)‐Symmetric Bis(Boronic Esters) by Zweifel Olefinations Linne, Yannick Schönwald, Axel Weißbach, Sebastian Kalesse, Markus Chemistry Communications anti‐Configured 1,3‐dimethyl deoxypropionate motifs are important sub structures in natural products. Herein, we describe a bidirectional approach for the rapid construction of natural products featuring such motifs by using C (2)‐symmetrical 1,3‐bis(boronic esters). As for its application in convergent syntheses it was important to establish a selective mono‐Zweifel olefination we describe the scope and limitations by using different 1,3‐bis(boronic esters) and nucleophiles. This protocol takes advantage of the combination of the Hoppe–Matteson–Zweifel chemistry, which was elegantly put into practice by Aggarwal et al. In order to show its applicability the total syntheses of two natural products, serricornin and (+)‐invictolide, were performed. John Wiley and Sons Inc. 2020-06-03 2020-06-26 /pmc/articles/PMC7384159/ /pubmed/32068298 http://dx.doi.org/10.1002/chem.202000599 Text en © 2020 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/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
Linne, Yannick
Schönwald, Axel
Weißbach, Sebastian
Kalesse, Markus
Desymmetrization of C (2)‐Symmetric Bis(Boronic Esters) by Zweifel Olefinations
title Desymmetrization of C (2)‐Symmetric Bis(Boronic Esters) by Zweifel Olefinations
title_full Desymmetrization of C (2)‐Symmetric Bis(Boronic Esters) by Zweifel Olefinations
title_fullStr Desymmetrization of C (2)‐Symmetric Bis(Boronic Esters) by Zweifel Olefinations
title_full_unstemmed Desymmetrization of C (2)‐Symmetric Bis(Boronic Esters) by Zweifel Olefinations
title_short Desymmetrization of C (2)‐Symmetric Bis(Boronic Esters) by Zweifel Olefinations
title_sort desymmetrization of c (2)‐symmetric bis(boronic esters) by zweifel olefinations
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7384159/
https://www.ncbi.nlm.nih.gov/pubmed/32068298
http://dx.doi.org/10.1002/chem.202000599
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