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Desymmetrization of C -Symmetric Bis(Boronic Esters) by Zweifel Olefinations.
Linne, Yannick Schönwald, Axel Weißbach, Sebastian Kalesse, Markus
Linne, Yannick
Schönwald, Axel
Weißbach, Sebastian
Kalesse, Markus
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2020-06-03
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Abstract
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 C2 -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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Chemistry. 2020 Jun 26;26(36):7998-8002. doi: 10.1002/chem.202000599.
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en
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1521-3765
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Attribution-NonCommercial-ShareAlike 4.0 International